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Synthesis method of furazabol intermediate androstane-17alpha-methyl-17beta-hydroxyl-3-ketone

A technology of furazandolone and its synthesis method, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of similar product polarity, influence on product purity, difficulty in removal, etc., achieve short route, easy control of production process, and low production cost Effect

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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1. Preparation of compound 3-ethoxy-androst-3,5-dien-17-one

[0031] Add 100g of 4-androstenedione, 60ml of triethyl orthoformate, and 100ml of absolute ethanol into the reaction flask, stir for 30 minutes after the addition, then add 2.0g of pyridinium hydrobromide, and heat up at 35°C to 45°C for 6 hours Carry out etherification reaction; after the reaction is completed, cool down to below 5°C, add triethylamine dropwise to adjust the pH value to 7.0-7.5, and stir for 1 hour after addition; cool down to below 0°C, filter and dry to obtain 104.9g of compound 3-B Oxy-androst-3,5-dien-17-one.

[0032] 2. Preparation of Grignard

[0033] Add 600ml of tetrahydrofuran, 47.2g of magnesium chips, and 0.2g of iodine particles into the reaction bottle, stir and raise the temperature to 40°C, start slowly feeding in methyl chloride at 40°C to 45°C until the magnesium chips completely react and disappear, continue at 40°C to 45°C ℃ heat preservation reaction for 1 hour to prepa...

Embodiment 2

[0039] 1. Preparation of compound 3-ethoxy-androst-3,5-dien-17-one

[0040] Add 100g of 4-androstenedione, 50ml of triethyl orthoformate, and 120ml of absolute ethanol into the reaction flask, stir for 30 minutes after addition, then add 1.5g of pyridine hydrobromide, heat up at 40°C to 50°C for 7 hours Carry out etherification reaction; after the reaction is completed, cool down to below 5°C, add triethylamine dropwise to adjust the pH value to 7.0-7.5, and stir for 1 hour after addition; cool down to below 0°C, filter and dry to obtain 103.5g of compound 3-B Oxy-androst-3,5-dien-17-one.

[0041] 2. Preparation of Grignard

[0042] Add 560ml of 2-methyltetrahydrofuran, 62.1g of magnesium chips, and 0.2g of iodine particles into the reaction flask, stir and raise the temperature to 40°C, start slowly feeding methyl bromide from 40°C to 45°C until the magnesium chips completely react and disappear, continue at 40°C ~45°C heat preservation reaction for 1 hour to prepare Grigna...

Embodiment 3

[0048] 1. Preparation of compound 3-ethoxy-androst-3,5-dien-17-one

[0049] Add 100g of 4-androstenedione, 100ml of triethyl orthoformate, and 90ml of absolute ethanol into the reaction flask, stir for 30 minutes after addition, then add 2g of pyridine hydrochloride, heat up at 30°C to 40°C for 9 hours to carry out etherification Reaction; after the reaction is complete, cool down to below 5°C, add dropwise triethylamine to adjust the pH value to 7.0-7.5, and stir for 1 hour after addition; cool down to below 0°C, filter and dry to obtain 102.0g of compound 3-ethoxy- Androst-3,5-dien-17-one.

[0050] 2. Preparation of Grignard

[0051] Add 600ml of ether and 40.8g of magnesium chips into the reaction bottle, stir and raise the temperature to 30°C, then slowly add methyl iodide dropwise from 30°C to 32°C until the magnesium chips are completely reacted and disappear, and continue the reflux reaction for 1 hour to obtain the Grignard reagent , cooled to below 10°C for later us...

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Abstract

The invention provides a synthesis method of a furazabol intermediate androstane-17alpha-methyl-17beta-hydroxyl-3-ketone. The method comprises the steps that 4-androstenedione (for short, 4AD) is usedas a raw material and subjected to 3-keto alkene etherification and 17-keto grignard addition; then, after grignard addition, acid hydrolysis is not conducted, a 5-ethylenic bond catalytic hydrogenation reaction is conducted at first, and finally 3-alkene ester and 17-dual hydrolysis are conducted to prepare the compound androstane-17alpha-methyl-17beta-hydroxyl-3-ketone, wherein the HPLC purityis above 99.0%. According to the method, the route is simple and short, the production technology is easily controlled, the method is environmentally friendly, the production cost is low, and the synthesis method is suitable for industrial large-scale production.

Description

technical field [0001] The present invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing a furazandrolone intermediate androsta-17α-methyl-17β-hydroxyl-3-one. Background technique [0002] Furazabol (17α-methyl-17β-hydroxy-5α-androstane (2,3-C) furazan), also known as Quzhishu and Furazabol, its structural formula is: [0003] . [0004] Furazanhydrol is an anabolic hormone drug, which can promote the synthesis of protein in the body and inhibit its catabolism. It also has the effect of lowering blood lipids and is suitable for hyperlipidemia and atherosclerosis. The traditional synthesis process of furazanhydrol intermediate androst-17α-methyl-17β-hydroxy-3-one is to obtain di Alkenes and dienes undergo reactions such as oximation, Beckmann rearrangement, acid hydrolysis, alkali hydrolysis, and catalytic hydrogenation to obtain epiandrosterone, and then prepare the target product through Grignard, additi...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0037
Inventor 廖俊曾建华刘玉亭付林李桂莲
Owner HUAZHONG PHARMA
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