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17-methyl-5 alpha-androstane-16-olefin-3-ketone and preparation method

A technology of methylandrosterone and methyl, which is applied in the field of organic chemical synthesis, achieves the effects of high synthesis purity, convenient operation and ingenious utilization

Inactive Publication Date: 2005-01-12
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the synthesis of methylandrosterone and its derivatives, there is no literature or patent report at home and abroad

Method used

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  • 17-methyl-5 alpha-androstane-16-olefin-3-ketone and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of Methylandrosterone Using Minandrolone as Raw Material

[0019] Dissolve 100 g of metandrolone in 100 mL of acetic anhydride, add 5 g of phosphoric acid, and stir at 60° C. for 1 hour. After the reaction was completed, it was poured into 5 L of water under stirring, allowed to stand, and filtered to obtain 93 g of a crude product of methylandrosterone. The crude product was recrystallized from ethanol to obtain 85 g of methylandrosterone. MS(m / z)286(M + ); m.p.143~144°C; Assay: 99.7% (HPLC).

Embodiment 2

[0021] Preparation of Methylandrosterone Using Minandrolone as Raw Material

[0022] Dissolve 100 g of metandrolone in 100 mL of propionic anhydride, add 5 g of p-toluenesulfonic acid, and stir at 80° C. for 1 hour. After the reaction was completed, it was poured into 5 L of water under stirring, allowed to stand, and filtered to obtain 93 g of a crude product of methylandrosterone. The crude product was recrystallized from ethanol to obtain 85 g of methylandrosterone. MS(m / z)286(M + ); m.p.143~144°C; Assay: 99.7% (HPLC).

Embodiment 3

[0024] Preparation of Methylandrosterone Using Minandrolone as Raw Material

[0025] Dissolve 100 g of metandrolone in 100 mL of heptanoic anhydride, add 5 g of phosphoric acid, and stir at 60-80°C for 1 hour. After the reaction was completed, it was poured into 5 L of water under stirring, allowed to stand, and filtered to obtain 93 g of a crude product of methylandrosterone. The crude product was recrystallized from ethanol to obtain 85 g of methylandrosterone. MS(m / z)286(M + ); m.p.143~144°C; Assay: 99.7% (HPLC).

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Abstract

The invention belongs to the field of organic chemical synthesis technology, and relates to a compound methylene androsterone (17-methyl-5 alpha-androst-16-ene-3-ketone) and its preparation method. Said invention uses mestanolone (17 beta-hydroxy-17-alpha-methyl-5-alpha-androstane-3-keton) as raw material, and makes it undergo the process of dehydraton reaction to obtain the invented methylene androsterone. The raw material of said invention is cheap and easily available, the acetic anhydride can be used as anhydrating agent, and the new compound methylene androsterone with high purity can be synthesized, and its synthetic method is simple and convenient.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a compound 17-methyl-5α-androst-16-en-3-one (methylandrosterone) and a preparation method thereof. Background technique [0002] With the improvement of living standards, people's awareness of self-health care is constantly improving, and it is expected that the market will introduce safe and effective new health care products. 17-methyl-5α-androst-16-en-3-one (methylandrosterone) is a better male hormone or anabolic hormone, and its biggest advantage is that it is not easily metabolized by the liver in the body. For the synthesis of methylandrosterone and its derivatives, there are no literature or patent reports at home and abroad. Contents of the invention [0003] The purpose of the present invention is to provide a new compound 17-methyl-5α-androst-16-en-3-one (also known as methylandrosterone) with simple and convenient synthesis method and high overall yield and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 张沪跃陈燕
Owner FUDAN UNIV
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