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Preparation method of 5alpha-androstanedion

A technology for androstanedione and compounds, which is applied in the field of preparation of 5α-androstanedione, can solve problems such as long steps and environmental pollution, and achieve the effects of low cost, easy availability of raw materials, and simple process operation

Active Publication Date: 2014-04-30
YICHENG GOTO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 5α-androstanedione is a key intermediate for the production of dozens of steroid hormones such as androstanolone, mesterolone, and primobolone. The existing process uses diosgenin as a raw material. Elimination, oximation, Beckmann rearrangement, hydrolysis, hydrogenation, oxidation and other reaction preparations, the method has long steps, and a large amount of chromium-containing wastewater is produced in the process of preparing diene from diosgenin, which causes great pollution to the environment

Method used

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  • Preparation method of 5alpha-androstanedion
  • Preparation method of 5alpha-androstanedion
  • Preparation method of 5alpha-androstanedion

Examples

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Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: The preparation method of this 5α-androstanedione adopts the following specific process steps, and the raw materials can be purchased from Danjiangkou Gongbio Co., Ltd.

[0022] (1) Reduction reaction:

[0023] Add 20.0g of the compound of formula (II) and 200ml of methanol into the reaction flask, stir the dissolved material, and cool down to 5°C; add once every 10 minutes, and add 4.5g of potassium borohydride in 3 batches; , TLC (thin layer chromatography) detects that there is no raw material point in the reaction; add an appropriate amount of glacial acetic acid dropwise to adjust the pH to 7.0, steam the methanol under reduced pressure below 70 degrees, pour into 800ml water for water analysis, stir for 30 minutes, suction filter, and a large amount of solids Washed with water, dried at 70°C to constant weight to obtain 20.0 g of the compound of formula (III) in the form of white powder, with a yield of 100.0%.

[0024] (2) Hydrogenation reaction:

[...

Embodiment 2

[0028] Example 2: The preparation method of this 5α-androstanedione adopts the following specific process steps.

[0029] (1) Reduction reaction:

[0030] Add 20.0g of the compound of formula (II) and 240ml of methanol into the reaction flask, stir and dissolve the material, cool down to 0°C, add once every 10 minutes, add 5.0g of potassium borohydride in 3 batches, and keep warm for 2 hours after adding , TLC detects that there is no raw material point in the reaction, add an appropriate amount of glacial acetic acid dropwise to adjust the pH to 7.0, distill methanol under reduced pressure below 70 degrees, pour into 800ml water for water analysis, stir for 30 minutes, suction filter, wash the solid with a large amount of water, and dry at 70 degrees to Constant weight was obtained to obtain 20.0 g of the compound of formula (III) as a white powder, with a yield of 100.0%.

[0031] (2) Hydrogenation reaction:

[0032] Add 20.0g of the compound of formula (III) and 300ml of ...

Embodiment 3

[0035] Embodiment 3: The preparation method of this 5α-androstanedione adopts the following specific process steps.

[0036] (1) Reduction reaction:

[0037] Add 20.0g of compound of formula (II) and 100ml of ethanol into the reaction flask, stir and dissolve the material, cool down to 20°C, add once every 10 minutes, add 2.0g of sodium borohydride in 3 batches, and keep warm for 2 hours after adding , TLC detects that there is no raw material point in the reaction, add an appropriate amount of glacial acetic acid dropwise to adjust the pH to 7.0, evaporate ethanol under reduced pressure below 70 degrees, pour 800ml of water into water, stir for 30 minutes, suction filter, wash the solid with a large amount of water, and dry it at 70 degrees to Constant weight was obtained to obtain 20.0 g of the compound of formula (III) as a white powder, with a yield of 100.0%.

[0038] (2) Hydrogenation reaction:

[0039] Add 20.0g of the compound of formula (III) and 160ml of methanol i...

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Abstract

The invention discloses a preparation method of 5alpha-androstanedion. The method comprises steps of a reduction reaction, a hydrogenation reaction and an oxidation reaction. The chemical synthesis method for preparing 5alpha-androstanedion avoids the disadvantages of long middle route, high danger, low yield and serious environmental pollution of a traditional production method. Compared to the traditional production method, the method provided by the invention has easily controlled reaction conditions, simple operations, high yield and reduced cost, and the yield of refined product is more than 70% in weight. The raw materials used in the method can be obtained by fermentation of phytosterols, which have wide source and low price; therefore, the method has the characteristics of easily available raw materials and low cost.

Description

technical field [0001] The invention relates to a preparation method of 5α-androstanedione. Background technique [0002] 5α-androstanedione is a key intermediate for the production of dozens of steroid hormones such as androstanolone, mesterolone, and primobolone. The existing process uses diosgenin as a raw material. Elimination, oximation, Beckmann rearrangement, hydrolysis, hydrogenation, oxidation and other reaction preparations, the method has long steps, and a large amount of chromium-containing waste water is produced in the process of preparing diene from diosgenin, which causes great pollution to the environment. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a simple and environment-friendly preparation method of 5α-androstanedione. [0004] In order to solve the problems of the technologies described above, 5α-androstanedione shown in formula (I) of the present invention, [0005] [0006] The m...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 潘高峰贺一君系祖斌
Owner YICHENG GOTO PHARMA
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