Preparation method of androst-4-ene-6beta,19-epoxy-3,17-dione

A technology of androsteroids and epoxy, applied in the direction of steroids, organic chemistry, etc., can solve the problems of expensive raw materials and the environment, and achieve the effects of low price, reduced environmental pollution, and high yield

Active Publication Date: 2015-06-24
EAST CHINA NORMAL UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention solves the high price of raw materials in the preparation of existing androst-4-ene-6β,19-epoxy-3,17-dione and the environmental problems in the process of obtaining raw materials through the following technical solutions

Method used

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  • Preparation method of androst-4-ene-6beta,19-epoxy-3,17-dione

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Embodiment 1

[0047] Embodiment 1: the method for preparing androst-4-ene-6β,19-epoxy-3,17-dione

[0048] The by-product androst-5-ene-3α-hydroxyl-17-one produced in the production process of 19-norandrost-4-ene-3,17-dione is used as the starting material and protected at the 3-position , epoxidation, epoxy ring opening, 6,19-position ring closure / 3-position hydrolysis, oxidation-dehydration five-step reaction to prepare androst-4-ene-6β,19-epoxy-3,17-di ketone. Specifically include the following steps:

[0049] Step 1: 3-Bit Protection

[0050] Add 50 g of androst-5-ene-3α-hydroxyl-17-one, 250 ml of toluene, 50 ml of acetic anhydride, and 25 ml of pyridine into the single-necked bottle, and react under reflux for 3 to 5 hours. Recover toluene, add 300ml of water and stir for 30min, suction filter and dry to obtain 56g of androst-5-en-17-one-3α-ol acetate. Yield: 98%.

[0051] Step 2: Epoxidation

[0052] Add 50g androst-5-en-17-one-3α-ol acetate, 650ml dichloromethane, 150ml tert-but...

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Abstract

The invention provides a preparation method of androst-4-ene-6beta,19-epoxy-3,17-dione. The androst-4-ene-6beta,19-epoxy-3,17-dione is prepared from androst-5-ene-3alpha-hydroxyl-17-one through reactions in five steps, namely 3-site protection, epoxidation, epoxide ring-opening, 6,19-site cyclization/3-site hydrolysis and oxidation-dehydration. By-product (waste) generated from a process of synthesizing a steroid drug is effectively utilized, so that environmental pollution is relieved, and the androst-4-ene-6beta,19-epoxy-3,17-dione, which serves as an important intermediate product and is required in the process of synthesizing the steroid drug, is obtained. The preparation method disclosed by the invention is high in yield and low in cost.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a preparation method of androst-4-ene-6β,19-epoxy-3,17-dione. Background technique [0002] The compound androst-4-ene-6β,19-epoxy-3,17-dione is an important intermediate for the preparation of 19-hydroxy steroids and 19-nor steroids, and has shown importance in the preparation of family planning drugs The application value, such as the anti-early pregnancy drug mifepristone, the contraceptive drug norethindrone series, telapristone, norgestimate, etc. [0003] In the past few decades, most of the 19-hydroxy steroids and 19-nor steroids were produced from pregna-5,16-dien-3-ol acetate (commonly known as dienolone acetate) as raw materials. The important intermediate androst-5-en-17-one-3-ol acetate (commonly known as rearrangement) was obtained through the Beckmann rearrangement of ketoxime. [0004] [0005] The 5,6-position addition of the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCC07J71/0005
Inventor 汤杰丁旭郑学军戴龙华杨帆张峥斌张汝金
Owner EAST CHINA NORMAL UNIV
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