1-hydroxyadamantanon-4-one preparation method

IPC classes for russian patent 1-hydroxyadamantanon-4-one preparation method (RU 2319688):

C07C49/513 -

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Invention provides a method for preparation of 1-hydroxyadamantanon-4-one (Kemantan), which can be used as immunostimulating drug effective to treat vascular system diseases, limbs autoimmune genesis extremities, tuberculosis, infection-allergic bronchial asthma, chronic aphthous stomatitis, herpes, as well as anticataleptic agent and intermediate for synthesis of 1,4-bifunctional derivatives of adamantane. Method comprises oxidation of adamantanone by means of sulfuric/nitric acid mixture in the form of complex oxidation-activating system including sulfuric, nitric, and acetic acids, molar ratio adamantanone/sulfuric acid/nitric acid/acetic acid being 1: (1.75) : (8.43-12.62) : (0.25-1). Process is carried out when stepwise raising temperature: first, at 35°C, nitric acid is measured out to reaction mass for 1-1.5 h, after which temperature is raised to 50-55°C for 12-16 h.

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1-hydroxyadamantanon-4-one preparation method / 2319688

Method of obtaining 1-hydroxyadamanthan-4-on / 2342358

Claimed invention relates to method of obtaining 1-hydroxyadamanthan-4-on, which is immuno-stimulating means, efficient for treatment of limbs vascular system diseases of autoimmune genesis, chronic stomatitis, herpes, etc. Method lies in catalytic oxidation of adamanthon-2. Here as oxidant agent, hydrobromous acid is used, which is generated in situ from carbon tetrabromide and water, and oxidation is performed in presence of catalysts - compounds of molybdenum Mo(CO)₆ or tungsten W(CO)_6, with molar ratio[Mo(CO)₆ or W(CO)₆]: [adamanthon-2]:[CBr₄]:[H₂O]=1:100:100:1000-4000 at temperature 140-160°C during 6-10 hours.

Method of producing 1-hydroxyadamantan-4-one / 2491270

Present invention relates to a method of producing 1-hydroxyadamantan-4-one, having immunostimulating action. The method involves oxidising adamantane with a mixture of CCl₄, water and an amide of propionic acid in the presence of a tungsten catalyst - W(CO)₆ for 6 hours at 150°C with molar ratio [W]:[AdH]:[CCl₄]:[CH₃CH₂CONH₂]:[H₂O] - 1:20:100:100:1000.

FIELD: organic synthesis and pharmaceutical industry.

SUBSTANCE: invention provides a method for preparation of 1-hydroxyadamantanon-4-one (Kemantan), which can be used as immunostimulating drug effective to treat vascular system diseases, limbs autoimmune genesis extremities, tuberculosis, infection-allergic bronchial asthma, chronic aphthous stomatitis, herpes, as well as anticataleptic agent and intermediate for synthesis of 1,4-bifunctional derivatives of adamantane. Method comprises oxidation of adamantanone by means of sulfuric/nitric acid mixture in the form of complex oxidation-activating system including sulfuric, nitric, and acetic acids, molar ratio adamantanone/sulfuric acid/nitric acid/acetic acid being 1: (1.75) : (8.43-12.62) : (0.25-1). Process is carried out when stepwise raising temperature: first, at 35°C, nitric acid is measured out to reaction mass for 1-1.5 h, after which temperature is raised to 50-55°C for 12-16 h.

EFFECT: increased yield of 1-hydroxyadamantanon-4-one and improved its purity.

7 ex

The invention relates to pharmaceutical industry and relates to a method of obtaining a 1-hydroxyadamantane-4-it (Kelantan) - immunostimulating agent, effective in the treatment of diseases of the vascular system, limbs autoimmune dysfunction, chronic bronchitis, tuberculosis, infectious-allergic bronchial asthma, chronic aphthous stomatitis, herpes, and is also used as anticatholicism means and intermediate for the synthesis of 1,4-bifunctional substituted adamantane.

There are several ways to obtain 1-hydroxyadamantane-4-it, including the oxidation of 2-hydroxyadamantane 70%sulfuric acid, followed by repeated extraction of the mixture of oxidation products and the additional oxidation of the obtained mixtures with chromic anhydride [H.W.Geluk, Tetrahedron, 24, s-5377, 1968]. The disadvantage is the low yield of the target product. The output in this case 1-hydroxyadamantane-4-it is not more than 25%.

In other ways the target product obtained by oxidation of adamantanone with chromic anhydride in acetic, propionic or triperoxonane acids [CS, patent No. 163671, CL SS 49/38, 1976], or by oxidation of adamantanone 12-fold excess of nitric acid [H.W.Geluk, Tetrahedron, 24, s-5368, 1968]. The disadvantages of these methods are low yields of final product, using large is icesta oxidants, fire explosive reagents.

The oxidation of adamantanone nitric acid, as shown by Helucom [H.W.Geluk, Tetrahedron Letters, No. 47, C-4476, 1971], form rather stable complexes with oxygen-containing adamantane derivatives with nitric acid. In terms of the allocation of product on the way, they are not completely decomposed, and getting rid of their impurities by crystallization also fails.

There is also known a method hydroxylation derivatives of adamantanone by a mixture of nitric and sulfuric acids in the presence of catalysts (sodium nitrite, manganese dioxide). The reaction is carried out mainly at 35°C, the reaction product is extracted with chloroform and allocate it after evaporation of the solvent [RU NO. 2104994 SS 49/487, 1998.02.20].

The disadvantage of this method of synthesis is the use of a considerable excess of 67.7%nitric acid of 3.46 mol, a 94.6%sulfuric acid - representing 22.06 mole and 0,8125 mol of sodium nitrate (as catalyst) on 1 mol of adamantanone and relatively low output Kelantan - 72%.

The closest analogue is the way hydroxylation derivatives aminoadamantana and oxidation of adamantanone by a mixture of nitric and sulfuric acids [SU inventor's certificate No. 974757, SS 49/24, SS 45/00, 1995.09.27]. The reaction is carried out mainly at 20°C. the Reaction mass by this method, after dilution with water, n is italist 40%sodium hydroxide solution, extracted with chloroform and isolated product after evaporation of the solvent. The disadvantage of this method is the low productivity due to low response speed, and complex instrumentation process due to the formation in the form of a precipitate of a large number of salts after alkalizing, which complicates the extraction of the target product.

The technical result of our proposed method is to develop a technologically advanced method of producing 1-hydroxyadamantane-4-it is with high yield and purity.

The technical result is achieved by oxidation of adamantanone using a mixture of sulfuric and nitric acids, with use of the complex oxidation-activating system, including sulfuric, nitric, acetic acid at a molar ratio:adamantane:nitric acid:sulfuric acid:acetic acid 1:1,75-2:8,43-12,62:0.25-1, and the process is carried out at step increase in temperature, first at 35°With metered into the reaction mass nitric acid for a period of 1-1 .5 hours, then increase the temperature to 50-55°and within 12-16 hours.

To reduce the amount of acidic waste and improving the selectivity of the oxidation process to a known system containing nitric and sulfuric acid (used for Kelantan) proposed to add acetic acid,

The speed and selectivity of the process can increase due to an improved homogenization of the reaction mixture and education "softer" oxidative particles of nitrone-cation solvated mixture of acetic and sulfuric acids. This results in improved yield and purity of the target product, improves the manufacturability of the process.

Conducting the reaction in a stepwise temperature increases initially at a temperature of 35°justified by the fact that when adding nitric acid 15-30 minutes, it begins to leak response education adamantoise cation (exothermic reaction) in this regard, it is necessary to control the temperature of the speed of the dosing acid within 1-1 .5 hours.

The choice of temperature range due to the fact that at the reaction temperature below 50°there is incomplete conversion of adamantanone and decreases the yield of the target product, and when the temperature rises above 55°there is also a decrease of the output 1-hydroxyadamantane-4-it from leaking further oxidation leading to the formation of trudnosgoraemyh products. The optimal duration of the reaction is 12-16 hours. Decrease or increase the length reduces the yield of the target product. When using acetic acid in a molar ratio of less than 0.25 to 1 mol of adamantanone n is observed a significant reduction in the degree of conversion source adamantanone. When the ratio of acetic acid above equimolar also observed a decrease in output due to the difficulty of the selection of the target product.

When studying the effect of the content of nitric acid in the reaction mass to the output of Kelantan we have found that when using a molar ratio adamantane:nitric acid less than 1:1,75 observed a significant reduction of the yield of the target product and increase the duration of the process.

The discovered patterns can be explained by the fact that the oxidation of adamantanone nitric acid, as shown by Helucom [H.W.Geluk, Tetrahedron Letters, No. 47, C-4476, 1971], form rather stable complexes with oxygen-containing adamantane derivatives with nitric acid in a molar ratio of 1:1. With increasing molar ratio adamantane:nitric acid above 1:2 there was a decrease of the yield of the desired product due to the formation of side products pereokislenie of adamantanone, soluble in water.

When studying the effect of the content of sulfuric acid in the reaction mass on the yield of the target product, we have found that using a molar ratio adamantane:sulfuric acid is less than 1:8,43 reduces the yield of the desired product due to the reduction of the pH and the increase of this ratio above 1:br12.62 also p is nijaat yield of the target product, because excessive acidity of the environment leads to peroxidation of the source reagent.

The novelty of the invention lies in the fact that they use a complex oxidation-activating system containing nitric, sulfuric, acetic acid. Due to this it is possible to increase the selectivity of the process due to an improved homogenization of the reaction mixture and education "softer" oxidative particles of nitrone-cation solvated mixture of acetic and sulfuric acids. This results in improved yield and purity of the target product, improves the manufacturability of the process.

The method is implemented as follows. To a solution of sulfuric acid or acetic acid is added gradually adamantane and maintaining the temperature not above 35°C, was added dropwise nitric acid for 1-1,5 hours. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C. Maintain the reaction mass in 12-16 hours, then poured on to ice, filtered off unreacted adamantane, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°C to stop the allocation of nitrogen oxides within 2-4 hours. Weakly acidic reaction mass (pH 5-6) is filtered and then the filtrate is extracted Kelantan with methylene chloride. The solvent is evaporated and get the target product output 65-87,4%.

Example 1. the solution in the 95.8 ml (1,80 mole) of 94.6%sulfuric acid and 4.6 ml (range : 0.08 mole) of acetic acid is gradually added 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, incubated for 12 hours, poured onto 200 g of ice, filtered 1.2 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and get 22,3 g Kelantan, the yield of 84.0%, TPL 318-320°C (recrystallized from CCl₄). The purity of Kelantan 98,3-99,0% (according to GC). The molar ratio of reagents:adamantane:nitric acid:sulfuric acid:acetic acid: 1:1,75:11,25:0,5.

Example 2. To the solution of the 95.8 ml (1,80 mole) of 94.6%sulfuric acid and 2.3 ml (0.04 mol) of acetic acid is gradually added 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, incubated for 12 hours, poured onto 200 g of ice, filtered 4,2 g adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml METI what inflorida, the solvent is evaporated and get a 20.2 g Kelantan, output 76,1%, TPL 318-320°C (recrystallized from CCl₄). The purity of Kelantan 97,3-98,0% (according to GC). The molar ratio of the reagents adamantane:nitric acid:sulfuric acid:acetic acid 1:1,75:11,25:0,25.

Example 3. To the solution of the 95.8 ml (1,80 mole) of 94.6%sulfuric acid 8,76 ml (0,16 mol) of acetic acid is gradually added 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, incubated for 12 hours, poured onto 200 g of ice, filtered off 0.8 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and get 22,4 g Kelantan, the yield of 84.3%, TPL 318-320°C (recrystallized from CCl₄). The purity of 98.3-99,0% (according to GC). The molar ratio of reagents:adamantane:nitric acid:sulfuric acid:acetic acid: 1:1,75:11,25:1.

Example 4. To the solution in 72 ml of 1.35 mol) of 94.6%sulfuric acid and 4.6 ml (range : 0.08 mole) of acetic acid is gradually added 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise during the course the e 1-1,5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, maintain the reaction mass 12 hours, poured onto 200 g of ice, filtered 5,4 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and obtain 17.3 g of Kelantan, the output of 65.1%, TPL 318-320°C (recrystallized from CCl₄). The purity of Kelantan 98,3% (according to GC). The molar ratio of reagents:adamantane:nitric acid:sulfuric acid:acetic acid 1:1,75:8,43:0,5.

Example 5. To a solution of 107 ml (2,02 mole) of 94.6%sulfuric acid and 4.6 ml (range : 0.08 mole) of acetic acid are added gradually, 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, incubated for 12 hours, poured onto 200 g of ice, filtered off 0.8 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and get 23,2 g Kelantan, the output of which is 87.4%, TPL 318-320° (paracrystalline the see of CCl ₄). The purity of Kelantan 98,7% (according to GC). The molar ratio of the reagents adamantane:nitric acid:sulfuric acid:acetic acid 1:1,75: 12,62:0,5.

Example 6. To the solution of the 95.8 ml (1,80 mole) of 94.6%sulfuric acid and 4.6 ml (range : 0.08 mole) of acetic acid are added gradually, 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours of 21.7 ml of 0.32 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of the reaction mass was raised to 50-55°C, incubated for 12 hours, poured onto 200 g of ice, filtered off 1.0 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and get 21 g of Kelantan, output 79,1%, TPL 318-320°C (recrystallized from CCl₄). The purity of 98.3-99,0% (according to GC). The molar ratio of reagents:adamantane:nitric acid:sulfuric acid:acetic acid 1:2:11,25:0,5.

Example 7. To the solution of the 95.8 ml (1,80 mole) of 94.6%sulfuric acid and 4.6 ml (range : 0.08 mole) of acetic acid are added gradually, 24 g (0,16 mol) of adamantanone and maintaining the temperature not above 35°C, was added dropwise within 1-1 .5 hours 19,0 ml (0,28 mol) 66,2%nitric acid. After adding all of nitric acid, the temperature of reaction the th mass raised to 50-55° C, maintain the reaction mass 16 hours, poured onto 200 g of ice, filtered off 0.8 g of adamantanone, the filtrate is neutralized with sodium hydroxide, keeping the temperature 50-55°before the termination of the allocation of nitrogen oxides (2-4 hours), extracted with 3 times 100 ml of methylene chloride, the solvent evaporated and get 22,9 g Kelantan, the yield of 86.2 per cent, TPL 318-320°C (recrystallized from CCl₄). The purity of Kelantan 98,3-99,0% (according to GC). Molar ratio of reactants:adamantane:nitric acid:sulfuric acid:acetic acid 1:1,75:11,25:0,5.

Conclusions: Thus, the developed technological method of synthesis of 1-hydroxyadamantane-4-it, which makes it possible to reduce the consumption of sulfuric acid at 45% and increase the yield of the target product from 72 to 87.4 per cent compared with the prototype.

A method of obtaining a 1-hydroxyadamantane-4-she oxidation of adamantanone using a mixture of sulfuric and nitric acids, characterized in that use complex oxidation-activating system consisting of sulphuric, nitric and acetic acid at a molar ratio adamantane: nitric acid: sulfuric acid: acetic acid equal to 1:1,75-2:8,43-12,62:0,25-1, moreover, the process is carried out at step increase in temperature, first at 35°With metered into the reaction mass nitric acid for a period of 1-1 .5 hours, then increase the temperature to 50-55°during the 12-6 o'clock