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Preparation method of 5alpha-androstane-3,17-dione

A technology of androstane and androstane, which is applied in the field of preparation of 5α-androstane-3,17-dione, can solve the problems of high production cost, environmental pollution, by-product generation, etc., and achieve low production cost , The process route is short and the effect of ensuring the yield level

Pending Publication Date: 2019-12-13
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In order to overcome the above-mentioned deficiencies of the prior art, the present invention provides a method for preparing 5α-androstane-3,17-dione, which solves the existing problems in the preparation of 5α-androstane-17-hydroxyl-3-one High production costs, serious environmental pollution, and problems such as by-products

Method used

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  • Preparation method of 5alpha-androstane-3,17-dione

Examples

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Embodiment 1

[0038] A preparation method of 5α-androstane-3,17-dione, specifically comprising the following steps:

[0039] Step 1: Preparation of compound 3-ethoxy-androst-3,5-dien-17-one wet material: add 100g of 4-androstenedione, 60ml of triethyl orthoformate, 100ml of absolute ethanol into the reaction flask After the addition, stir for 30 minutes, then add 2.0 g of pyridine hydrobromide, heat up at 35°C to 45°C and keep warm for 6 hours for etherification reaction; after the reaction is completed, cool down to below 5°C, and drop triethylamine to adjust the pH 7.0 to 7.5, heat up and reflux for 1 hour after adding; cool down to below 0°C, filter to obtain 107.8g of compound 3-ethoxy-androst-3,5-dien-17-one wet material;

[0040] Step 2: Prepare a solution of 3-ethoxy-3-androstene-17-one: add 25g of 3-ethoxy-androstene-17-one obtained in the previous step to the reaction bottle -ketone wet material, 625ml methyl alcohol, 125ml dichloromethane, after stirring evenly, dropwise add the ...

Embodiment 2

[0043] A preparation method of 5α-androstane-3,17-dione, specifically comprising the following steps:

[0044] Step 1: Preparation of compound 3-ethoxy-androst-3,5-dien-17-one Wet material: add 100g of 4-androstenedione, 50ml of triethyl orthoformate, 120ml of absolute ethanol into the reaction flask After the addition, stir for 30 minutes, then add 1.5g of pyridine hydrobromide, heat up at 40°C to 50°C and keep warm for 7 hours for etherification reaction; after the reaction is completed, cool down to below 5°C, and drop triethylamine to adjust the pH value to 7.0 to 7.5, heat up and reflux for 1 hour after adding; cool down to below 0°C, filter to obtain 108.1g of compound 3-ethoxy-androst-3,5-dien-17-one wet material;

[0045] Step 2: Add 30g of 3-ethoxy-androst-3,5-dien-17-one wet material, 600ml of methanol, and 150ml of dichloromethane into the reaction bottle, stir well and add hydrogen dropwise The methanol solution of sodium oxide adjusts the pH value to 8.5-9.0, add...

Embodiment 3

[0048] A preparation method of 5α-androstane-3,17-dione, specifically comprising the following steps:

[0049] Step 1: Add 100g of 4-androstenedione, 100ml of triethyl orthoformate, and 90ml of absolute ethanol into the reaction flask, stir for 30 minutes after the addition, then add 2g of pyridine hydrochloride, heat up at 30°C to 40°C for 9 hours Carry out etherification reaction; after the reaction is completed, cool down to below 5°C, add dropwise triethylamine to adjust the pH value to 7.0-7.5, and then raise the temperature and reflux for 1 hour; cool down to below 0°C, and filter to obtain 106.9g of compound 3-ethoxy Base-androst-3,5-dien-17-one wet material.

[0050] Step 2: Add 25g of 3-ethoxy-androst-3,5-dien-17-one, 625ml of methanol, and 125ml of methylene chloride obtained in the previous step into the reaction bottle, stir well and add potassium hydroxide dropwise Adjust the pH value of the methanol solution to 7.5-8.0, add 2.5g of palladium-carbon catalyst with...

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Abstract

The invention relates to a preparation method of 5alpha-androstane-3,17-dione. The method specifically comprises the following steps: 1, carrying out an etherification reaction on 4-androstenedione, triethyl orthoformate and anhydrous ethanol in the presence of an etherification catalyst, and performing post-treatment after the etherification reaction is completed in order to prepare a compoundwet 3-ethoxy-3,5-androstadien-17-one; 2, adding a the wet 3-ethoxy-3,5-androstadien-17-one into a methanol-dichloromethane mixed solvent, performing uniform stirring, adjusting the pH value of the obtained solution, carrying out a catalytic hydrogenation reaction under the action of a palladium-carbon catalyst, and filtering out the catalyst after the reaction is finished in order to obtain a 3-ethoxy-3-androstene-17-one solution; and 3, carrying out a hydrolysis reaction on the 3-ethoxy-3-androstene-17-tone solution and an acid, removing the solvent after the hydrolysis reaction is finished,and carrying out filtering, water washing and drying to obtain the 5alpha-androstane-3,17-dione. The method has the advantages of short process route, easily controlled production process, environmental friendliness, low production cost, and suitableness for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of 5α-androstane-3,17-dione. Background technique [0002] 5α-Androstane-3,17-dione, formula C 19 h 28 o 2 , molecular weight 288.42, its structural formula is: [0003] [0004] 5α-androstane-3,17-dione is a key intermediate in the production of dozens of steroid hormone drugs such as androstanolone, minandrolone, anadrol, mesterolone, flazabol, and stanozolol. The market application is very extensive. [0005] The existing technology is to use diosgenin as raw material to obtain dienes through reactions such as ring opening, acylation, oxidation, hydrolysis, and elimination, and to obtain dehydrogenation of dienes through oximation, Beckmann rearrangement, acid hydrolysis, and alkali hydrolysis. Epiandrosterone, and then through catalytic hydrogenation to obtain epiandrosterone, and then through oxidation to prepare the target product. ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 廖俊刘玉亭付林曾建华徐明琴
Owner HUAZHONG PHARMA
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