Preparation method of androst-2-en-17-one

A technology of androstenedione and androstene is applied in the field of preparation of steroid hormone drug intermediates, can solve the problems of large side reactions, large amount of by-products, low synthesis yield and the like in the elimination reaction, and achieves good product quality and high reaction efficiency. Selective and source-rich effects

Inactive Publication Date: 2019-04-19
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, in view of the existing process technology of androst-2-en-17-one, the side reactions of the elimination reaction are large, the amount of by-products is large, the impurities are difficult to refine, the synthesis yield is low, and the production cost is high. Many defects such as the purpose of the present invention It is to provide a new preparation method of androst-2-en-17-one to significantly reduce the production cost of androst-2-en-17-one

Method used

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  • Preparation method of androst-2-en-17-one

Examples

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Effect test

Embodiment 1

[0029] A, preparation of solid-phase acid catalyst:

[0030] In a 1000ml three-neck flask, add 100g of solid silica gel, 400ml of pure water, 200ml of pure water and 5g of p-toluenesulfonic acid, and stir the adsorption reaction at 30-35°C for 3-4 hours. After the reaction, evaporate under reduced pressure. Remove water to nearly dry, take out and dry to obtain 99.8g of solid phase acid catalyst, moisture content 2.6%, weight yield 99.8%;

[0031] B, 4-androstenedione to prepare epiandrosterone:

[0032] Such as image 3 As shown, using 4-androstenedione as a raw material, epiandrosterone was synthesized through a three-step reaction of etherification protection reaction, palladium carbon-catalyzed hydrogenation reduction reaction, and acid-catalyzed hydrolysis deprotection reaction. Specifically, 4-androstenedione is firstly used as a raw material to react with triethyl orthoformate to generate an etherified product protected by etherification at the 3-position, and the eth...

Embodiment 2

[0036] A, preparation of solid-phase acid catalyst:

[0037] In a 1000ml three-necked flask, add 100g of solid alumina, 400ml of pure water, 200ml of pure water and 5g of sulfuric acid, and stir the adsorption reaction at 30-35°C for 3-4 hours. After the reaction, evaporate the water under reduced pressure. To nearly dry, take out and dry to obtain 99.6g of solid-phase alkali catalyst, moisture content 2.8%, weight yield 99.6%;

[0038] B, 4-androstenedione to prepare epiandrosterone:

[0039] Such as image 3 As shown, using 4-androstenedione as a raw material, epiandrosterone was synthesized through a three-step reaction of etherification protection reaction, palladium carbon-catalyzed hydrogenation reduction reaction, and acid-catalyzed hydrolysis deprotection reaction. Specifically, 4-androstenedione is firstly used as a raw material to react with triethyl orthoformate to generate an etherified product protected by etherification at the 3-position, and the etherified pro...

Embodiment 3

[0043] A, preparation of solid-phase acid catalyst:

[0044] In a 1000ml three-necked flask, add 100g of solid magnesium sulfate powder, 400ml of pure water, 200ml of pure water and 5g of nitric acid, and stir the adsorption reaction at 30-35°C for 3-4 hours. After the reaction, evaporate it under reduced pressure. Water to nearly dry, take out and dry to obtain 99.8g of solid-phase acid catalyst, moisture content 2.1%, weight yield 99.8%;

[0045] B, 4-androstenedione to prepare epiandrosterone:

[0046] Such as image 3 As shown, using 4-androstenedione as a raw material, epiandrosterone was synthesized through a three-step reaction of etherification protection reaction, palladium carbon-catalyzed hydrogenation reduction reaction, and acid-catalyzed hydrolysis deprotection reaction. Specifically, 4-androstenedione is firstly used as a raw material to react with triethyl orthoformate to generate an etherified product protected by etherification at the 3-position, and the et...

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Abstract

The invention discloses a preparation method of androst-2-en-17-one. The method comprises the steps that 4-androstenedione is adopted as a raw material, three-step reactions of a protective reaction,a reduction reaction and a deprotection reaction are adopted for synthesizing epiandrosterone, in an organic solvent, a carrier solid phase acid catalyst soaked with acid is used for catalyzing, epiandrosterone dehydration is performed to eliminate 3-bit hydroxyls in molecules, and a target product is obtained. 4-androstenedione obtained by phytosterol extracted from a soybean oil deodorization distillate through the modern fermentation technology is adopted as a raw material; 4-androstenedione is subjected to the three-step reactions to synthesize a key intermediate epiandrosterone, and raw materials are abundant in source and low in price. The epiandrosterone is used for preparing a target product, compared with a traditional method, a synthetic route is cut into a one-step reaction fromtwo-step reactions, the method is economical and environmentally friendly, and production and operation are easier. By adopting the carrier solid phase acid catalyst soaked with acid for catalyzing,an oligomer makes indirect contact with the acid catalyst, the reactions are mild and stable, the dehydration elimination reactions are performed in the thermodynamics stable 2,3-bit directions, and the reaction selectivity is good.

Description

technical field [0001] The invention belongs to the preparation technology of steroid hormone drug intermediates, and specifically relates to a key intermediate androst-2-ene for the production of rocuronium bromide, vecuronium bromide and other common muscle-relaxing steroid hormone drugs Process for the preparation of -17-ones. Background technique [0002] Androst-2-en-17-one, also known as rocuronium bromide intermediate LK-2, is a general intermediate for the production of steroid hormone drugs. Using it as a raw material can produce various common muscle relaxant steroid hormone drugs such as rocuronium bromide and vecuronium bromide. Common muscle relaxant steroid hormone drugs such as rocuronium bromide and vecuronium bromide are important adjuvant drugs for anesthesia in surgical operations. Androst-2-en-17-one undergoes 6-step reactions such as 17-enol esterification, double epoxidation, ring opening with different alicyclic amines, reduction, diesterification, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 左前进吴来喜羊向新
Owner HUNAN KEREY BIOTECH
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