Preparation method of stanolone

A technology of androdonolone and androsterone, which is applied in the field of preparation technology of steroid hormone drugs, can solve problems such as complicated process operation, high production cost, and long synthesis route, and achieve wide sources of raw materials, reduced production cost, and short synthesis route Effect

Inactive Publication Date: 2017-03-15
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a new preparation method of androsandrolone, which solves the problems of expensive synthetic raw materials, long synthetic route, complicated process operation, difficult environmental protection treatment and high production cost in the traditional production process.

Method used

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  • Preparation method of stanolone
  • Preparation method of stanolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A. Preparation of ether compounds

[0024] In a 1000ml three-neck flask, add 100g 4AD, 200ml ethanol, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. After the reaction, add 3ml of pyridine, stirred for 20-25 minutes to neutralize the acid, then cooled the system to -5-0°C, stirred and crystallized for 2-3 hours, filtered with suction, washed with a small amount of ethanol, combined the washing liquid and the filtrate, recovered the solvent and used the crude product; filtered The cake was dried below 70°C to obtain 101.6 g of the ether compound, the HPLC content was 99.2%, and the weight yield was 101.6%.

[0025] B. Preparation of reduced products

[0026] In a 1000ml three-necked flask, add 100g of ether compound and 800ml of ethanol, stir and raise the temperature to 20-25°C, slowly add 12g of sodium borohydride, and finish adding in about 0.5-1.0 hours, then continue t...

Embodiment 2

[0032] A. Preparation of ether compounds

[0033] In a 1000ml three-neck flask, add 100g 4AD, 600ml dichloromethane, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. After TLC detects the end point of the reaction, add 3ml Pyridine, stir for 20-25 minutes to neutralize the acid, concentrate under reduced pressure, recover dichloromethane, lower the temperature, add 100ml of ethanol, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, filter with suction, wash with a small amount of ethanol , the washing solution and the filtrate were combined, the recovered solvent and the crude product were used mechanically; the filter cake was dried below 70°C to obtain 100.2g of etherified compound, the HPLC content was 99.4%, and the weight yield was 100.2%.

[0034] B. Preparation of reduced products

[0035] In a 1000ml three-neck flask, add 100g of ether compound and 800ml of methanol, stir and raise the temperature ...

Embodiment 3

[0041] A. Preparation of ether compounds

[0042] In a 1000ml three-neck flask, add 100g 4AD, 200ml ethanol, and 80ml triethyl orthoformate, inject 2g of HCl gas, seal it, keep it warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. , add 3ml of pyridine, stir for 20-25 minutes to neutralize the acid, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, filter with suction, wash with a small amount of ethanol, combine the lotion and filtrate, recover the solvent and use the crude product The filter cake was dried below 70°C to obtain 103.2g of etherified compound, the HPLC content was 99.1%, and the weight yield was 103.2%.

[0043] B. Preparation of reduced products

[0044] In a 1000ml three-necked flask, add 100g of ether compound and 800ml of methanol, stir to raise the temperature to 20-25°C, slowly add 12g of sodium borohydride, finish adding in 0.5-1.0 hours, continue to keep warm and stir for 2-3 hours, and detect by TLC ...

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Abstract

A preparation method of stanolone comprises the following steps: with 4-androstenedione (shortened as 4AD) as a raw material, firstly performing an acid-catalyzed reaction on the 4AD and triethyl orthoformate in an organic solvent to obtain etherate 3-ethoxy-androst-3,5-diene-17-one; then, adding the etherate into the organic solvent, adding metal borohydride as a reducing agent, and reducing a 17-one group in a molecule of the etherate into a hydroxyl group to obtain the 3-ethoxy-androst-3,5-diene-17-ol; then, dissolving a reduced product into the organic solvent, adding a hydrogenation reaction catalyst, selectively catalyzing a 5-position double bond in the molecule of the reduced product to obtain hydride 3-ethoxy-androst-3-ene-17-ol; finally, performing acid-catalyzed hydrolysis on the hydride in the organic solvent to obtain the stanolone. Compared with the conventional production method, the preparation method provided by the invention has the advantages as follows: the raw material source is wide, the synthesis route is short, the preparation method is simple and environment-friendly in process, the product yield is high, the preparation method is economical and environment-friendly, the production cost is reduced by 35-40%, and the preparation method is very conductive to industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation technology of steroid hormone drugs, and in particular relates to a preparation method of androgen drug androgen. Background technique [0002] Andrandrolone, also known as dihydrotestosterone, is a male hormone drug, which is mainly used clinically to promote the development of male sexual organs and secondary sexual characteristics and maintain their normal functions. It can also be used to synthesize other advanced androgen drugs such as dehydrotestosterone, and the market application prospect is broad. The traditional production method of androsandrolone is to extract diosgenin from yam plant, after protection, oxidative cracking, and elimination, obtain the key intermediate - acetic acid pregnant dienolone (referred to as diene) as raw material, after oximation, Baker Mann rearrangement, reduction, alkali hydrolysis, oxidation, catalytic hydrogenation and other six-step reactions, the sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/007
Inventor 甘红星陈双胡爱国谢来宾
Owner HUNAN KEREY BIOTECH
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