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Preparation method of 5 alpha-androstane-3, 17-dione

A technology for androstane and diketone, applied in the field of organic chemical synthesis, can solve the problems of inability to effectively avoid isomer hydrogenation by-products, lack of hormone activity, failure to improve the purity of 5α hydrogenation products, etc., and to reduce the generation of , Guarantee the yield level, improve the effect of purity

Inactive Publication Date: 2020-03-06
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In order to realize the purpose of selective catalytic hydrogenation to prepare 5α hydrogenation products, the applicant of the present invention uses palladium charcoal, palladium / calcium carbonate as hydrogenation catalyst respectively, with methanol, ethanol, isopropanol etc. as hydrogenation reaction solvent, with caustic soda aqueous solution and hydrochloric acid Regulating the pH value of the reaction system (pH value ranges from 3.0 to 9.0) to carry out catalytic hydrogenation reactions of experimental batches with different factors and levels, failed to achieve the purpose of improving the purity of 5α hydrogenated products, and the maximum impurity content in the hydrogenated products obtained in experimental batches Still above 12%, unable to effectively avoid the generation of isomer hydrogenation by-products, and steroidal compounds with 5β-H structure have almost no hormonal activity

Method used

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  • Preparation method of 5 alpha-androstane-3, 17-dione
  • Preparation method of 5 alpha-androstane-3, 17-dione
  • Preparation method of 5 alpha-androstane-3, 17-dione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1. The preparation method of 17α-hydroxyl-17β-cyano-androst-4-en-3-one is as follows:

[0041] Add 100g of 4-androstenedione, 100ml of acetone cyanohydrin, 200ml of ethyl acetate and 20ml of triethylamine into the reaction flask, stir well and keep it warm at 60°C to 65°C for 20 hours to react; after the reaction is completed, evaporate to dryness under reduced pressure After all the solvents were added, methanol was added to entrain, and concentrated under reduced pressure to a paste; the temperature was lowered to below 5°C, filtered, and dried to obtain 106g of 17α-hydroxyl-17β-cyano-androst-4-en-3-one, weight Yield 106%.

[0042] 2. The preparation method of 17α-hydroxyl-17β-cyano-5-androstene-3-ethylene glycol ketal is as follows:

[0043] Add 20g of 17α-hydroxy-17β-cyano-androst-4-en-3-one, 0.6g of p-toluenesulfonic acid, 10ml of triethyl orthoformate, 20ml of ethylene glycol and 30ml of dichloromethane into the reaction flask, and stir well And keep warm at 33°...

Embodiment 2

[0050] 1. The preparation method of 17α-hydroxyl-17β-cyano-androst-4-en-3-one is as follows:

[0051] Add 100g of 4-androstenedione, 90ml of acetone cyanohydrin, 220ml of ethyl acetate and 15ml of diethylamine into the reaction bottle, stir well and keep it warm at 60°C to 65°C for 24 hours to react; after the reaction is completed, evaporate to dryness under reduced pressure After all the solvents were added, methanol was added to entrain, and concentrated under reduced pressure to a paste; the temperature was lowered to below 5°C, filtered and dried to obtain 105.9g of 17α-hydroxyl-17β-cyano-androst-4-en-3-one, The weight yield was 105.9%.

[0052] 2. The preparation method of 17α-hydroxyl-17β-cyano-5-androstene-3-ethylene glycol ketal is as follows

[0053] Add 20g17α-hydroxyl-17β-cyano-androst-4-en-3-one, 0.4g sulfosalicylic acid, 8ml triethyl orthoformate, 40ml ethylene glycol and 20ml dichloromethane into the reaction flask, stir After the reaction is completed, cool d...

Embodiment 3

[0060] 1. The preparation method of 17α-hydroxyl-17β-cyano-androst-4-en-3-one is as follows:

[0061] Add 100g of 4-androstenedione, 120ml of acetone cyanohydrin, 180ml of ethyl acetate and 30ml of diethylamine into the reaction bottle, stir well and keep it warm at 55°C to 60°C for 22 hours to react; after the reaction is completed, evaporate to dryness under reduced pressure After all the solvents were added, methanol was added to entrain, and concentrated under reduced pressure to a paste; the temperature was lowered to below 5°C, filtered and dried to obtain 106.5g of 17α-hydroxyl-17β-cyano-androst-4-en-3-one, The weight yield was 106.5%.

[0062] 2. The preparation method of 17α-hydroxyl-17β-cyano-5-androstene-3-ethylene glycol ketal is as follows:

[0063] Add 20g of 17α-hydroxy-17β-cyano-androst-4-en-3-one, 0.8g of p-toluenesulfonic acid, 20ml of triethyl orthoformate, 18ml of ethylene glycol and 40ml of chloroform into the reaction flask, and stir well And keep warm ...

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Abstract

The invention discloses a preparation method of 5 alpha-androstane-3, 17-dione. The method includes the steps of: taking 4-androstenedione as the raw material, carrying out 17-site keto hydroxycyaniding, 3-site keto ketal, 17-site hydroxycyanogen hydrolysis, 5, 6 double bond catalytic hydrogenation and 3-site ketal acid hydrolysis to obtain the compound 5 alpha-androstane-3, 17-dione. The method provided by the invention has the advantages of low production cost, high product purity and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of 5α-androstane-3,17-dione. Background technique [0002] 5α-Androstane-3,17-dione, formula C 19 h 28 o 2 , molecular weight 288.42, its structural formula is: [0003] [0004] 5α-androstane-3,17-dione is a key intermediate in the production of dozens of steroid hormone drugs such as androstanolone, minandrolone, anadrol, mesterolone, flazabol, and stanozolol. The market application is very extensive. [0005] The existing technology is to use diosgenin as raw material to obtain dienes through reactions such as ring opening, acylation, oxidation, hydrolysis, and elimination, and to obtain dehydrogenation of dienes through oximation, Beckmann rearrangement, acid hydrolysis, and alkali hydrolysis. Epiandrosterone, and then through catalytic hydrogenation to obtain epiandrosterone, and then through oxidation to prepare the target pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 廖俊刘玉亭付林曾建华朱小涛魏旭力田玉林
Owner HUAZHONG PHARMA
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