Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF2 Cites 3 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 5alpha-androstanedion
  • Preparation method of 5alpha-androstanedion
  • Preparation method of 5alpha-androstanedion

Examples

Experimental program
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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07J1/00
Inventor 潘高峰贺一君系祖斌
Owner YICHENG GOTO PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com