Preparation method of 5alpha-androstane-17-hydroxy-3-one

A technology of hydroxyl and androster, which is applied in the field of preparation of 5α-androst-17-hydroxy-3-one, can solve the problems of cumbersome process steps, intermediate structure changes, high production costs, etc., achieve short process routes and avoid intermediates Structural changes and low production costs

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

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Problems solved by technology

[0014] In order to overcome the above-mentioned deficiencies of the prior art, the invention provides a method for preparing 5α-androst-17-hydroxyl-3-one, which solves the existing problems in the preparation of 5α-androst-17-hydroxyl-3-one High production costs, serious environmental pollution, cumbersome process steps, and high temperature drying lead to changes in the intermediate structure, etc.

Method used

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  • Preparation method of 5alpha-androstane-17-hydroxy-3-one
  • Preparation method of 5alpha-androstane-17-hydroxy-3-one
  • Preparation method of 5alpha-androstane-17-hydroxy-3-one

Examples

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Embodiment 1

[0037] A preparation method of 5α-androst-17-hydroxyl-3-one, specifically comprising the following steps:

[0038] Step 1: Preparation of compound 3-ethoxy-androst-3,5-dien-17-one: 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 pyridine hydrobromide, raise the temperature at 35°C to 45°C and keep it warm for 6 hours to carry out the etherification reaction; 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;

[0039] Step 2: Prepare a solution of 3-ethoxy-3-androstene-17-one: add 625ml of methanol and 125ml of dichloromethane into the reaction bottle, stir well and add triethylamine dropwise to adjust the pH value to 8.0-8.5 , then drop into 25g of the 3-ethoxy-androst-3,5-diene-17-one wet material obtained by the previous step reaction, stir...

Embodiment 2

[0042] A preparation method of 5α-androst-17-hydroxyl-3-one, specifically comprising the following steps:

[0043] Step 1: Preparation of compound 3-ethoxy-androst-3,5-dien-17-one: add 100g 4-androstenedione, 50ml triethyl orthoformate, 120ml absolute ethanol into the reaction flask, Stir for 30 minutes after adding, then add 1.5g of pyridine hydrobromide, heat up at 40°C to 50°C for 7 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, 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;

[0044] Step 2: Prepare a solution of 3-ethoxy-3-androstene-17-one: add 600ml of methanol and 150ml of dichloromethane into the reaction bottle, stir evenly, add triethylamine dropwise to adjust the pH value to 8.5-9.0 , then drop into 30g of the 3-ethoxy-androst-3,5-dien-17-one wet ma...

Embodiment 3

[0047] A preparation method of 5α-androst-17-hydroxyl-3-one, specifically comprising the following steps:

[0048] Step 1: Preparation of compound 3-ethoxy-androst-3,5-dien-17-one: add 100g 4-androstenedione, 100ml triethyl orthoformate, 90ml absolute ethanol into the reaction flask, Stir for 30 minutes after the addition, then add 2g of pyridine hydrochloride, heat up at 30°C-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, After the addition, the temperature was raised to reflux for 1 hour; the temperature was lowered to below 0°C, and 106.9 g of compound 3-ethoxy-androst-3,5-dien-17-one wet material was obtained by filtration;

[0049] Step 2: Prepare a solution of 3-ethoxy-3-androstene-17-one: add 625ml of methanol and 125ml of dichloromethane into the reaction bottle, stir well and add triethylamine dropwise to adjust the pH value to 7.5-8.0 , then ...

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Abstract

The invention relates to a preparation method of 5alpha-androstane-17-hydroxy-3-one. 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 to prepare a compound wet 3-ethoxy-3,5-androstadien-17-one; 2, sequentially adding a protective reagent and the wet 3-ethoxy-3,5-androstadien-17-one into a methanol-dichloromethane mixed solvent, and then carrying out catalytic hydrogenation reaction under the action of a palladium-carbon catalyst to obtain a 3-ethoxy-3-androstene-17-one solution; and 3, adding a metal borohydride into the 3-ethoxy-3-androstene-17-one solution, carrying out a reduction reaction, adding an acid after the reduction reaction is finished, carry out a hydrolysis reaction, removing the solvent after the hydrolysis reaction is finished, and carrying out filtering, water washing, drying, and refining to obtain the 5alpha-androstane-17-hydroxy-3-one. 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-androst-17-hydroxyl-3-one. Background technique [0002] 5α-androst-17-hydroxy-3-one, formula C 19 h 30 o 2 , molecular weight 290.44, its structural formula is: [0003] [0004] 5α-Androst-17-Hydroxy-3-one is the key intermediate in the production of dozens of steroid hormone drugs such as Primobolan, Anadrol, Drostansterone, Mesterolone, Frazabol, Stanozolol, etc. Body, 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, then undergo catalytic hydrogenation reaction to obtain epiandrosterone, prepare androstanedione through oxid...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0022
Inventor 廖俊刘玉亭付林邬德琦冯蕾
Owner HUAZHONG PHARMA
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