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Preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone

A technology of methyl and hydroxyl, applied in the field of organic chemical synthesis, can solve the problems of similar polarity of products, affecting product purity, difficult to remove, etc., achieve low production cost, easy control of production process, and ensure the effect of yield level

Pending Publication Date: 2019-04-16
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of 17-position acidolysis and 3-keto-ene etherification deprotection at the same time, the next step of catalytic hydrogenation reaction is easy to introduce a The isomeric impurity of 5βH structure, which is extremely similar to the polarity of the product and difficult to remove, thus ultimately affecting the purity of the product

Method used

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  • Preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone
  • Preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone
  • Preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1. Preparation of compound 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal

[0034] Add 20g of methyltestosterone, 100ml of dichloromethane, 30ml of triethyl orthoformate, 40ml of ethylene glycol and 1ml of boron trifluoride ether into the reaction bottle, stir well and keep warm at 30°C to 35°C for 10 hours to react; after the reaction is completed , lower the temperature to below 5°C, add triethylamine dropwise to adjust the pH value to 7.0-7.5, and stir for 30 minutes after addition; evaporate all solvents under reduced pressure, entrain with 20ml methanol, concentrate under reduced pressure to a paste, add 20ml methanol Reflux for 30 minutes; cool down to below 5°C, filter and dry to obtain 22.1g of 5-androstene-17α-methyl-17β-hydroxy-3-ethylene glycol ketal;

[0035] 2. Preparation of the compound androst-17α-methyl-17β-hydroxyl-3-one

[0036]Add 20g of 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal, 320ml of methanol and 80ml of dichlor...

Embodiment 2

[0039] 1. Preparation of compound 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal

[0040] Add 20g of methyltestosterone, 80ml of chloroform, 40ml of triethyl orthoformate, 60ml of ethylene glycol and 2ml of boron trifluoride ether into the reaction bottle, stir well and keep warm at 30°C to 35°C for 9 hours to react; after the reaction is completed , lower the temperature to below 5°C, add triethylamine dropwise to adjust the pH value to 7.0-7.5, and stir for 30 minutes after addition; evaporate all solvents under reduced pressure, entrain with 20ml methanol, concentrate under reduced pressure to a paste, add 20ml methanol Reflux for 30 minutes; cool down to below 5°C, filter and dry to obtain 22.3g of 5-androstene-17α-methyl-17β-hydroxy-3-ethylene glycol ketal;

[0041] 2. Preparation of the compound androst-17α-methyl-17β-hydroxyl-3-one

[0042] Add 20g of 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal, 270ml of methanol and 90ml of dichlorometha...

Embodiment 3

[0045] 1. Preparation of compound 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal

[0046] Add 20g of methyltestosterone, 120ml of dichloromethane, 60ml of triethyl orthoformate, 60ml of ethylene glycol and 1ml of boron trifluoride ether into the reaction bottle, stir well and keep warm at 30°C to 35°C for 9 hours to react; , lower the temperature to below 5°C, add triethylamine dropwise to adjust the pH value to 7.0-7.5, and stir for 30 minutes after addition; evaporate all solvents under reduced pressure, entrain with 20ml methanol, concentrate under reduced pressure to a paste, add 20ml methanol Reflux for 30 minutes; cool down to below 5°C, filter and dry to obtain 22.0g of 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene glycol ketal;

[0047] 2. Preparation of the compound androst-17α-methyl-17β-hydroxyl-3-one

[0048] Add 20g of 5-androstene-17α-methyl-17β-hydroxyl-3-ethylene ketal, 200ml of methanol and 100ml of dichloromethane into the reaction flask, sti...

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PUM

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Abstract

The invention provides a preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone. According to the method, methyltestosterone as a raw material is subjected to ketalation, catalytic hydrogenation and a hydrolysis reaction to obtain the androstane-17alpha-methyl-17beta-hydroxy-3-ketone. The method has the advantages that the process is simple and clear, the production cost is low, the purity of the product is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of androst-17α-methyl-17β-hydroxyl-3-one. Background technique [0002] Androst-17α-methyl-17β-hydroxy-3-one, formula C 20 h 32 o 2 , molecular weight 304.47, its structural formula is: [0003] [0004] Androst-17α-methyl-17β-hydroxy-3-one is a key intermediate in the production of dozens of steroid hormone drugs such as Anadrol, Mesterolone, Frazabol, Stanozolol, etc. It is widely used in the market. [0005] The traditional production method of androst-17α-methyl-17β-hydroxyl-3-one is to use diosgenin as raw material, through ring-opening, acylation, oxidation, hydrolysis, elimination and other reactions to obtain dienes, and dienes are oximated , Beckmann rearrangement, acid hydrolysis, alkali hydrolysis, catalytic hydrogenation and other reactions to obtain epiandrosterone, and then prepare the target product through Grignard, add...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0037
Inventor 廖俊曾建华刘玉亭王勇付林
Owner HUAZHONG PHARMA
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