Method for preparing 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to chemistry of adamantane derivatives, namely, to a novel method for synthesis of 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes of the general formula: wherein Hal means bromine atom (Br); R means hydrogen atom (H), -CH3, -C2H5, -C3H7; Hal means Br; R means -CH3; R1 means -CH3; Hal means chlorine atom (Cl); R means Cl; R1 means Cl that can be used as intermediate compounds used for synthesis of some biologically active substances. Method involves interaction of 1,3-dehydroadamantane with α-halogenalkane carboxylic acids ethyl esters chosen from the following group: ethyl-2-bromoacetate, ethyl-2-bromopropionate, ethyl-2-bromobutyrate, ethyl-2-bromovalerate, ethyl-2-bromo-2-methylpropionate and ethyl-2,2,2-trichloroacetate taken in the mole ratio = 1:(3-5), respectively, in the parent α-halogenalkane carboxylic acid ethyl esters medium, at temperature 50-60°C for 4-6 h. Invention provides expanding assortment of chemical compounds, in particular, synthesis of novel 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes with the high yield.

EFFECT: improved method of synthesis.

6 ex

 

The invention relates to the chemistry of adamantane derivatives, namely to a new method for the preparation of 3-halogen-1-(etoxycarbonyl)alkyladamantanes General formula:

where Hal=Br, R=H: R1=H, CH3With2H5With3H7;

Hal=Br, R=CH3: R1=CH3; Hal=Cl, R=Cl: R1=Cl;

which may be of interest as intermediates in the synthesis of some biologically active substances.

A method of obtaining bromine derivatives adamantylidene acids, in which the bromine atom is not in the 3rd position adamant-1-ilen fragment, as in α-position of the hydrocarbon side chain, which consists in the treatment of 1-adamantylamine acid with thionyl chloride and the interaction of the obtained acid chloride with bromine and subsequent hydrolysis of the acid chloride α-bromo-1-adamantylamine acid. It α-bromo-1-adamantylamine acid [A.S. 910605 SS 101/04. Publ. 07.03.82,]. The output of this product reaches 70%.

The disadvantage of this method is that it allows you to get only one derivative (α-bromo-1-adamantylamine acid), and this method does not lead to obtaining substances claimed structural formulas.

A method of obtaining α-amino-(substituted-1)-acetic acid and α-amino-(substituted-1)-propiona the Oh of the acid when using α -bromo-1-adamantylamine acid and (substituted-1)-propionic acid. Similar to previous, after halogenation source halides J2(Br2and subsequent ammonolysis of a 19% solution of NH4OH in methyl alcohol produced products with the release of 75-85% [Synthesis, decomposition and chemical transformation α-amino acids adamantanol range / Krasutsky P.A., Novikova M.I., Semenov I.G.//Chemistry and technology of Organoelement intermediates and polymers. Proc. Dokl. The scientific. Conference, Volgograd, 1984/Volge. - Volgograd, 1984. - S.138-141].

This method does not lead to obtaining substances claimed structural formulas.

Know the use of (substituted-2)-acetic acid to obtain α-amino-(substituted-2)-acetic acid. From the source (substituted-2)-acetic acid get its ethyl ester, which is then halogenous, receiving α-bromo-(substituted-2)-acetic acid. The obtained bromo derivatives reacts with ammonia, resulting in α-amino-(substituted-2)-acetic acid [Hromadko Soja. α-Amino-2-adamantylessigsaure und verhafren zu your herstellung // Patent DE 2521895. - 1976].

This method also does not receive the substance of the claimed structural formulas.

Closest to the proposed invention is a method of synthesis of 3-bromo-1-adamantanecarbonyl [Stetter H., Mayer J. Chem. Ber. 1962, 95, 667] and 3-bromo-1-adamant luxusni acid [K. Bott Chem. Ber. 1968, 101, 564-573] by direct synthesized 1-adamantanecarbonyl or 1-adamantylamine acids in the presence or in the absence of a catalyst.

The disadvantage of this method is the limited number of synthesized compounds, so that in this way it is impossible to obtain the claimed compounds of structural formulas.

The task of the invention is to develop technological molestating method of synthesis of 3-halogen-1-(etoxycarbonyl)alkyladamantanes proceeding with a high output source adamantane.

The technical result is the expansion of the range of chemical compounds, in particular obtaining new 3-halogen-1-(etoxycarbonyl)alkyladamantanes with high output.

The technical result is achieved in a new method of obtaining 3-halogen-1-(etoxycarbonyl)alkyladamantanes General formula

where Hal=Br, R=H: R1=H, CH3With2H5With3H7;

Hal=Br, R=CH3: R1=CH3; Hal=Cl, R=C1: R1=Cl.

by reacting 1,3-dehydroalanine with ethyl esters α-halogenocarboxylic acids from a number of: ethyl 2-bromoacetate, ethyl 2-bromopropionate, ethyl 2-bromobutyrate, ethyl 2-bromovalerate, ethyl 2-bromo-2-methylpropionate, ethyl 2,2,2-trichloroacetate when the molar ratios of the reactants equal the ACC is respectively 1:3-5, in the source environment ethyl esters α-halogenocarboxylic acid, at a temperature of 50-60°C for 4-6 hours.

where Hal=Br, R=H: R1=H, CH3With2H5With3H7;

Hal=Br, R=CH3: R1=CH3; Hal=Cl, R=Cl: R1=Cl.

The essence of the method is the reaction for the preparation of 3-halogen-1-(etoxycarbonyl)alkyladamantanes on the reactions of addition to 1,3-dehydroalanine (1,3-DCA) of the corresponding ethyl esters α-halogenocarboxylic acids.

The reaction is based on previously unknown properties of 1,3-dehydroalanine to interact liaison carbon-halogen bonds in ethyl esters α-halogenocarboxylic acids. The reaction is unknown, as the literature contains no information about the interaction of 1,3-dehydroalanine with ethyl esters α-halogenocarboxylic acids or related compounds. Interaction is possible due to high mobility of the halogen on the air α-halogenocarboxylic acids generated electron-acceptor effect located at the nearest methylene (retinovoy) the carboxyl group of the fragment. The high nucleophilicity of 1,3-dehydroalanine allows you to get the addition products in high yields in a fairly mild conditions.

The method is a trail which accordingly.

To a 3-5-fold molar excess of ethyl ether α-halogenecarbonate acid is poured a solution of 1,3-dehydroalanine in boiling inert solvent (diethyl ether), which is then removed from the reaction mixture by distillation. A mixture of 1,3-dehydroalanine and ethyl ether α-halogenecarbonate acid is heated for 4-6 hours at a temperature of 50-60°C, after which the excess of the initial ethyl ester α-halogenecarbonate acid is distilled off. It is possible to regenerate the original ethyl esters α-halogenocarboxylic acids by distillation from the reaction mixture and the organization of recycling with the addition of the calculated amount of fresh ethyl ester α-halogenecarbonate acid. Synthesized 3-halogen-1-(etoxycarbonyl)alkyladamantanes purified by vacuum distillation. The outputs of these products are 75-87%.

We have studied a number of regularities flow between 1,3-dehydroalanine with ethyl esters α-halogenocarboxylic acids. As studies have shown, the optimal and technological condition of carrying out the reactions of addition of ethyl esters α-halogenocarboxylic acid to 1,3-dehydroalanine is its implementation in an environment of excess of original ethyl esters α-halogenocarboxylic acid at a molar with which the compared 1,3-dehydroalanine:ethyl ether α -halogenecarbonate acid=1:3-5. Less excess has resulted in a slight decrease of the yield of the target products due to possible homopolymerization 1,3-dehydroalanine and incomplete conversion. Further increase in the content of ethyl ether α-halogenecarbonate acid did not affect the yield of target products was inappropriate. The optimal reaction temperature is 50-60°C. lowering the temperature to room leads to a strong increase in the duration of this interaction and the reduction of the yield of target products, while further increasing along with the acceleration of the reaction leads to side reactions accession 1,3-dehydroalanine to ethyl ether α-halogenecarbonate acid is not due to C-Br, and the C-H α-carbon atom. The optimal treatment duration is 4-6 hours. The reduction of the reaction time leads to incomplete conversion of 1,3-dehydroalanine and reduce the yield of the target product. The increase in reaction time is impractical due to the full conversion of 1,3-dehydroalanine.

The structure of the synthesized compounds are confirmed by the H-NMR, mass spectroscopy and elemental analysis.

The invention is illustrated by the following examples:

Example 1.

Ethyl ester α-(3-bromo-1-substituted)acetic acid

To 14.7 g (0.088 mol) of ethyl ether α-bromoxynil acid (ethyl 2-bromoacetate) in a dry nitrogen atmosphere at room temperature was added dropwise a solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA: ethyl ether α-bromoxynil acid=1:4) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 55-60°C for 5 hours, after which the excess ethyl ester α-bromoxynil acid is removed by distillation, the residue is distilled in vacuum and get 5.27 g (0.075 mol, 79.6%) ethyl ester α-(3-bromo-1-substituted)acetic acid. TKip=146-147°C / 2 mm RT. Art. n20D) 1.5310. An NMR spectrum1H δ, ppm: 1.25 t (3H, CH3), 1.35-2.30 (14N, substituted-1,3), 2.5 (2H, CH2C(O)), 4.11 kV (2H, -och2-). Mass spectrum, m/e, I, %: 272, 15% [M-C2H5]; 214, 8%, [AdBr]; 193, 1% [AdCH2COO]; 134, 100%, [1,3-Ad], 79-80, 29%, [Br]. Found, %: 55.45, H 6.98, Br at 26.64. C14H21O2Br. Calculated, %: C 55.81, H 6.97, Br at 26.58.

Example 2.

Ethyl ester α-(3-bromo-1-substituted)propionic acid.

To 16.72 g (0.0924 mol) ethyl ester α-bromopropionic acid (ethyl 2-bromopropionate) in a dry nitrogen atmosphere at room temperature was added dropwise a solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine (zootoxin the e 1,3-DCA:ethyl ether α -bromopropionic acid=1:4.2) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 60°C for 4.5 hours, after which the excess ethyl ester α-bromopropionic acid is removed by distillation, the residue is distilled in vacuum and get 5.61 g (0.0178 mol, 81%) of ethyl ether α-(3-bromo-1-substituted)propionic acid. TKip=144-145°C/0.5 mm Hg n20D1.5218. An NMR spectrum1H δ, ppm: 1.00 t (3H, CH3); 1.20 (3H, CH3(eff.)); 1.40-2.30 (14N, 1,3-substituted, 1H, SNA(O)), 4.07 kV (2H, -och2-). Found, %: C 57.15, H 7.28, Br 25.34. With15H23O2Br. Calculated, %: C 57.14, H 7.30, Br 25.39.

Example 3.

Ethyl ester α-(3-bromo-1-substituted)butyric acid.

To 14.62 g (0.075 mol) of ethyl ether α-pamakani acid (ethyl-2-bromobutyrate) in a dry nitrogen atmosphere at room temperature was added dropwise a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA: ethyl ether α-pamakani acid=1:5) in 15 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 60°C for 6 hours, the excess ethyl ester α-pamakani acid removed by distillation, the residue is distilled in vacuum and obtain 3.74 g (0.0114 mol, 75.8%) Atila the CSOs ether α -(3-bromo-1-substituted)butyric acid. TKip=170-172°C/3 mm Hg n20D1.5199. An NMR spectrum1N, δ, ppm: 0.77 t (3H, CH3); 1.29 t (3H, CH3(eff.)); 1.35-2.3 (14N, 1,3-substituted; 1H CHC(O)2H, -CH2-), 4.20 kV (2H, -och2-). Found, %: 58.33, H 7.58, Br 24.37. With16H25O2Br. Calculated, %: C with 58.36, H 7.60, Br at 24.32.

Example 4. Ethyl ester α-(3-bromo-1-substituted)valerianic acid.

To 13.8 g (0.066 mol) of ethyl ether α-bombalurina acid (ethyl 2-bromovalerate) in a dry nitrogen atmosphere at room temperature was added dropwise a solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine in 15 ml of absolute diethyl ether (ratio of 1,3-DCA: ethyl ether α-bombalurina acid=1:3), after which the solvent is distilled off, the reaction mixture was kept at a temperature of 55-60°C for 5 hours, after which the excess ethyl ester α-bombalurina acid is removed by distillation, the residue is distilled in vacuum and obtain 5.7 g (0.0166 mol, 75.5%) ethyl ester α-(3-bromo-1-substituted)valerianic acid. TKip=178-179°C / 2 mm Hg n20D1.5182. An NMR spectrum1N, δ, ppm: 0.88 t (3H, CH3); 1.21 t (3H, CH3(eff.)); 1.35-2.30 (14N, 1,3-substituted, 1H, SNA(OH); 4H, -(CH2)2-), 4.10 kV (2H, -och2-). Found, %: C 59.50, N 9.59, Br 23.33. With17H O2Br. Calculated, %: C 59.47, N 9.62, Br 23.32.

Example 5.

Ethyl ester α-(3-bromo-1-substituted)-2-methylpropionic acid

To 17.92 g (0.11 mol) of ethyl ether α-bromo-2-methylpropionic acid (ethyl 2-bromo-2-methylpropionate) in a dry nitrogen atmosphere at room temperature was added dropwise a solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA; ethyl ester α-bromo-2-methylpropionic acid=1:5) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 50-60°C for 5 hours after which the excess ethyl ester α-bromo-1-methylpropionic acid is removed by distillation, the residue is distilled in vacuum and obtain 6.06 g (0.0192 mol, 87.5%), ethyl ester α-(3-bromo-1-substituted)-2-methylpropionic acid. TKip=159-160°C/2 mm Hg n20D1.5240. An NMR spectrum1N, δ, ppm: 1.05 (6N, 2CH3); 1.20 (3H, CH3(eff.)); 1.52-2.35 (14N, 1,3-substituted), 4.08 kV (2H, -och2-). Found, %: C 58.32, H 7.57, Br 24.35. C16H25O2Br. Calculated, %: C with 58.36, H 7.60, Br at 24.32.

Example 6.

Ethyl ester α-(3-chloro-1-substituted)-2,2-dichloracetic acid

To 16.8 g (0.088 mol) of ethyl ester of trichloroacetic acid (ethyl 2,2,2-trichloroacetate) in the atmosphere is dry and the PTA at room temperature was added dropwise a solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute diethyl ether (ratio of 1,3-DCA:ethyl ester of trichloroacetic acid=1:4). When mixing, there is a slight exothermic effect. Upon completion of the reaction the solvent is distilled off, the reaction mixture was kept at a temperature of 60°C for 4 hours, after which the excess ethyl ester of trichloroacetic acid is removed by distillation, the residue is distilled in vacuum and get 5.96 g (0.0183 mol, 83.2%) ethyl ester α-(3-chloro-1-substituted)-2,2-dichloracetic acid. TKip=181-183°C/5 mm Hg n20D1.5332. An NMR spectrum1H δ, ppm: 1.27 t (3H, CH3(eff.)); 1.50-2.30 (14N, 1,3-substituted), 4.34 kV (2H, -och2-). Mass spectrum, m/e, 1,%: 133, 26%, [1,3-Ad]; 169, 100%, [ClAd]; 253, 15%, [ClAdCCl2]; 289, 12%, [M-Cl]. Found, %: C 51.64, H 5.82, Cl 32.76. C14H19O2Cl3. Calculated, %: C 51.61, H 5.84, Cl 32.72.

Conclusions

Developed a new one-step method for the preparation of 3-halogen-1-(etoxycarbonyl)alkyladamantanes to obtain the claimed compounds of structural formula with high yields. The structure of the obtained compounds was confirmed mass, NMR1N-spectroscopy and elemental analysis.

Method for the preparation of 3-halogen-1-(etoxycarbonyl)alkyladamantanes General formula:

where Hal=Br, R=H:R1=H, CH3C2H3With3H7;

Hal=Br, R=CH3:R1=CH3; Hal=Cl, R=Cl:R1=Cl,

which consists in interaction of the tvii 1,3-dehydroalanine with ethyl esters α -halogenocarboxylic acids from a number of: ethyl 2-bromoacetate, ethyl 2-bromopropionate, ethyl 2-bromobutyrate, ethyl 2-bromovalerate, ethyl 2-bromo-2-methylpropionate, ethyl 2,2,2-trichloroacetate when the molar ratios of the reagents, respectively 1:3-5, in the environment of the original ethyl esters α-halogenocarboxylic acid, at a temperature of 50-60°C for 4-6 hours



 

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11 cl, 7 ex

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17 cl, 13 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to chemistry of adamantane derivatives, namely, to a novel method for synthesis of 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes of the general formula: wherein Hal means bromine atom (Br); R means hydrogen atom (H), -CH3, -C2H5, -C3H7; Hal means Br; R means -CH3; R1 means -CH3; Hal means chlorine atom (Cl); R means Cl; R1 means Cl that can be used as intermediate compounds used for synthesis of some biologically active substances. Method involves interaction of 1,3-dehydroadamantane with α-halogenalkane carboxylic acids ethyl esters chosen from the following group: ethyl-2-bromoacetate, ethyl-2-bromopropionate, ethyl-2-bromobutyrate, ethyl-2-bromovalerate, ethyl-2-bromo-2-methylpropionate and ethyl-2,2,2-trichloroacetate taken in the mole ratio = 1:(3-5), respectively, in the parent α-halogenalkane carboxylic acid ethyl esters medium, at temperature 50-60°C for 4-6 h. Invention provides expanding assortment of chemical compounds, in particular, synthesis of novel 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes with the high yield.

EFFECT: improved method of synthesis.

6 ex

FIELD: chemistry.

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1 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a stereoselective method of obtaining a fluorinated molecule having a fluorine atom with asymmetrical carbon (R) or (S) configuration in the α position relative an ester or ketone group in which: (i) a fluorosulphite compound of given configuration on C* which carries the fluorosulphite group of formula (III) is put into a reactor, (2i) the fluorosulphite compound is thermally decomposed in the presence of a nucleophilic catalyst which contains a tertiary nitrogen atom, at temperature ranging from 60°C to 180°C, (3i) a fluorinated molecule having reverse configuration of formula (IV) is obtained, provided that: -R1 denotes alkyl, alkenyl, alkynyl, where these groups can be straight or branched, aryl, cycloalkyl, alkylcycloalkyl, CO2R5, - (CH2)n-CO2R5, -COR5, -SOR5, -SO2R5, where n is an integer from 1 to 12, R5 denotes hydrogen or alkyl, alkenyl, alkynyl, where these groups can be straight or branched, cycloalkyl, alkylcycloalkyl, aryl, particularly substituted aryl; R1 can also form an aromatic or not a heterocycle containing, instead of one or more carbon atoms, one or more heteroatoms selected from oxygen, sulphur or nitrogen; -R2 denotes hydrogen or a group corresponding to definition given for R1; - R1 and R2 are different; - R3 denotes hydrogen or a R6 or -OR6 group, where R6 is selected a list given for R5; where R6 and R1 can be identical or different.

EFFECT: use of the present method enables to stereoselectively obtain fluorinated molecules with good output using cheap and reagents which do not lead to large amounts of effluent.

40 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: method involves combined synthesis of 1'-alkyl-1'-ethylformyl-(C60-Ih)[5,6]fullero[2':,3':1,9]cyclopropanes and 1'a-alkyl-1'a ethylformyl-1'a-carba-1'(2')a-homo(C60-Ih)[5,6]fullerenes of general formula

, where Alkyl =Et, i-Pr, i-Bu, Bn, where C60-fullerene reacts with α-alkyldiazoacetic ether of general formula N2C(alkyl)COOEt, where alkyl = Et, i-Pr, i-Bu, Bn, in o-dichlorobenzene in the presence of a three-component catalyst {Pd(acac)2:2PPh3:4Et3Al}, taken in molar ratio C60-fullerene: α-alkyldiazoacetic ether: Pd(acac)2:PPh3:Et3Al=0.01:(0.05-0.15):(0.0015-0.0025):(0.003-0.005):(0.006-0.01), preferably 0.01:0.1:0.002:0.004:0.008, at temperature of 40°C for 0.25-1.0 hours. 1'-alkyl-1'-ethylformyl-(C60-1h)[5,6]fullero[2',3':1,9]cyclopropanes (1) and 1'a-alkyl-1'a ethylformyl-1'a-carba-1'(2')a-homo(C60-Ih)[5,6]fullerenes (2) are obtained in ratio of 1:1 and total output of 55-79%.

EFFECT: high yield.

1 tbl, 10 ex

FIELD: process engineering.

SUBSTANCE: invention relates to catalysis. Proposed catalyst contains alcoholate of alkaline metal in solution of monohydroxy alcohol. Note here that said monohydroxy alcohol represents isobutyl alcohol, while alcoholate of alkaline metal represents potassium isobutyl with the following ratio of components in wt %: potassium isobutyl - 10-25; isobutyl alcohol - 75-90.

EFFECT: production of biodiesel from various vegetable oils, simplified process.

18 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to versions of a method of producing a phenylpropionic acid derivative of general formula: or salt thereof, where R2a is a methoxy group or ethoxy group; R3b is a cyclopentyl group and R5 is a methyl group which can be substituted with one or more phenyl groups, or an oxygen-containing heterocyclic group used as an intermediate compound during synthesis of 3-{5-[4-(cyclpentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl}propionic acid (T-5224), having anti-arthritic action and osteoclast inhibitory action. One of the versions of the method involves reaction of a benzophenol derivative of general formula: 3 , where R2a and R3b are as described above, or salts thereof with a 6-(halogenmethyl)-1,2-benzisoxazol-3(2H)-one derivative of general formula: , where R5 is as described above, and X is a halogen atom. The disclosed method can be used as a method for simple and safe synthesis of T-5224 with high output. The invention also relates to methods of producing intermediate compounds and novel intermediate compounds.

EFFECT: high efficiency of the composition.

28 cl, 23 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method of producing functionally substituted fullerenes used as complexing agents, sorbents and biologically active compounds. The method of producing 1'a-methyl-1'a-ethylformyl-1'a-carba-1'(2')a-homo(C60-Ih)[5,6]fullerene of formula (1) is characterised by that C60-fullerene reacts with α-methyldiazoacetic ester of formula N2C(Me)COOEt, in α-dichlorobenzene in the presence of a three-component catalyst {Pd(acac)2 : 2PPh3:4Et3Al}, taken in molar ratio C60:α-methyldiazoacetic ester :Pd(acac)2:PPh3:Et3Al = 0.01:(0.01-0.10):(0.0015-0.0025):(0.003-0.005):(0.006-0.01), preferably 0.01:0.05:0.002:0.004:0.008 at temperature 40°C for 0.25-1.0 hours.

EFFECT: desired product is obtained with 58-86% output.

1 tbl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to chemistry of adamantane derivatives, namely, to a novel method for synthesis of 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes of the general formula: wherein Hal means bromine atom (Br); R means hydrogen atom (H), -CH3, -C2H5, -C3H7; Hal means Br; R means -CH3; R1 means -CH3; Hal means chlorine atom (Cl); R means Cl; R1 means Cl that can be used as intermediate compounds used for synthesis of some biologically active substances. Method involves interaction of 1,3-dehydroadamantane with α-halogenalkane carboxylic acids ethyl esters chosen from the following group: ethyl-2-bromoacetate, ethyl-2-bromopropionate, ethyl-2-bromobutyrate, ethyl-2-bromovalerate, ethyl-2-bromo-2-methylpropionate and ethyl-2,2,2-trichloroacetate taken in the mole ratio = 1:(3-5), respectively, in the parent α-halogenalkane carboxylic acid ethyl esters medium, at temperature 50-60°C for 4-6 h. Invention provides expanding assortment of chemical compounds, in particular, synthesis of novel 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes with the high yield.

EFFECT: improved method of synthesis.

6 ex

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