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Preparation method of Stanolone

A technology of androsandrolone and compound, which is applied in the field of preparation of androsandrolone, can solve the problems of complex process route, easy to pollute the environment, produce more waste water, etc., and achieve the effect of simple process route, high purity and less pollutants

Inactive Publication Date: 2017-08-29
ZHEJIANG PURUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the extraction of diosgenin, oxidative cracking, Beckmann rearrangement, reduction, alkali hydrolysis, oxidation reaction and other processes have complicated process routes, produce more wastewater, are difficult to treat, and are easy to pollute the environment.

Method used

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  • Preparation method of Stanolone
  • Preparation method of Stanolone
  • Preparation method of Stanolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In the embodiment of the present invention, a kind of preparation method of androsandrolone, the structural formula of described androsandrolone is as follows:

[0024] Its specific preparation method is as follows:

[0025] (1) Compound I reacts with acetone cyanohydrin or sodium cyanide to form compound II with a cyano group. When compound I reacts with acetone cyanohydrin or sodium cyanide, it needs to be used under alkaline conditions. Potassium carbonate, sodium carbonate, triethylamine or sodium hydroxide to adjust pH = 8, temperature 30 degrees Celsius;

[0026] (2) Adjust the pH of the solution of Compound II to be acidic, use PTS, boron trifluoride or acetic acid solution to adjust the pH, and then use ethylene glycol and triethyl orthoformate to form a ketal; then adjust the solution to a strong alkaline Under the conditions, pH ≥ 13, let the cyano group drop, and finally generate compound III;

[0027] (3) Add sodium borohydride or potassium borohydride t...

Embodiment 2

[0033] In the embodiment of the present invention, a kind of preparation method of androsandrolone, the structural formula of described androsandrolone is as follows:

[0034] Its specific preparation method is as follows:

[0035] (1) Compound I reacts with acetone cyanohydrin or sodium cyanide to form compound II with a cyano group. When compound I reacts with acetone cyanohydrin or sodium cyanide, it needs to be used under alkaline conditions. Potassium carbonate, sodium carbonate, triethylamine or sodium hydroxide to adjust pH=9, temperature 35 degrees Celsius;

[0036] (2) Adjust the pH of the solution of Compound II to be acidic, use PTS, boron trifluoride or acetic acid solution to adjust the pH, and then use ethylene glycol and triethyl orthoformate to form a ketal; then adjust the solution to a strong alkaline Under the conditions, pH ≥ 13, let the cyano group drop, and finally generate compound III;

[0037] (3) Add sodium borohydride or potassium borohydride to ...

Embodiment 3

[0042] In the embodiment of the present invention, a kind of preparation method of androsandrolone, the structural formula of described androsandrolone is as follows:

[0043] Its specific preparation method is as follows:

[0044] (1) Compound I reacts with acetone cyanohydrin or sodium cyanide to form compound II with a cyano group. When compound I reacts with acetone cyanohydrin or sodium cyanide, it needs to be used under alkaline conditions. Potassium carbonate, sodium carbonate, triethylamine or sodium hydroxide to adjust pH=10, temperature 40 degrees Celsius;

[0045] (2) Adjust the pH of the solution of Compound II to be acidic, use PTS, boron trifluoride or acetic acid solution to adjust the pH, and then use ethylene glycol and triethyl orthoformate to form a ketal; then adjust the solution to a strong alkaline Under the conditions, pH ≥ 13, let the cyano group drop, and finally generate compound III;

[0046] (3) Add sodium borohydride or potassium borohydride to...

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Abstract

The invention discloses a preparation method of Stanolone, and the structure formula of the Stanolone is as shown in the specification. The preparation method is as follows: (1) addition reaction of a compound I with acetone cyanohydrin or sodium cyanide to obtain a compound II with a cyanogroup; (2) regulation of the pH of a solution of the compound II to acid, ketalation of the solution of the compound II with ethylene glycol and triethyl orthoformate, regulation of the pH of the solution to strong alkaline to remove the cyanogroup to finally produce a compound III; (3) reduction of 17-site keto group to hydroxy in the compound III by use of sodium borohydride or potassium borohydride for formation a compound IV; (4) addition of a catalyst to a solution of the compound IV, and hydrogenation to obtain a compound V; and (5) hydrolysis ketalation of the compound V in acetone under acidic conditions to obtain the target product stanolone. The process route of the method is simple, the stanolone is finally prepared based on the addition reaction, less pollution is produced, production efficiency is high, and the prepared stanolone has high purity.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a preparation method of androsandrolone. 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 the yam plant, through protection, oxidative cracking, and elimination, to obtain the key intermediate - acetic acid pregnant dienolone (diene for short) as raw material, through oximation, Baker Mann rearrangement, reduction, alkali hydrolysis, oxidation, catalytic hydrogenation and other six-step reaction. Among them, the extraction of diosgenin, oxidative cracking, Beckman...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0018
Inventor 徐润星张学忠王锦凯
Owner ZHEJIANG PURUI PHARMA
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