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New organic compound 4-androstene-3beta, 17 beta-diol bis (ethylcarbonyldioxy) ester and its prepn

A technology of organic compounds and androstene, which is applied in the field of new organic compounds and organic compound preparations, can solve the problems of low oral activity, liver danger, trouble, etc., and achieve the effect of high yield, good oral activity, and simple preparation process

Inactive Publication Date: 2002-09-25
EAST CHINA NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, an outstanding disadvantage of this compound is that the oral activity is too low. If it is taken as a health food in large doses, it will be troublesome and uneconomical; if the 17α-alkyl derivative with higher oral activity is taken, it will be potentially dangerous to the liver.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1. Dissolve 10g of 4-androstenediol in 150g of dichloromethane, N 2 protection, electromagnetic stirring, adding 50 g of triethylamine, slowly dropwise adding 40 g of ethyl chloroformate, controlling the reaction temperature at 50-60° C., and reacting for 5 hours. The reaction solution was washed 3 times with 15 g of 10% hydrochloric acid, 3 times with 15 g of saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 Dry, and remove the solvent under reduced pressure to obtain a crude product, which is separated by silica gel column chromatography, and the eluent is a mixed solution of petroleum ether and ethyl acetate, petroleum ether:ethyl acetate=10:1, and the product 4-androstene- 3β, 17β-diol bis(ethyl carbonate) 14.4g, yield 96%. m.p.110-112°C.

Embodiment 2

[0016] Example 2. Dissolve 10g of 4-androstenediol in 150g of dichloromethane, N 2 protection, electromagnetic stirring, adding 40 g of triethylamine, slowly adding 30 g of ethyl chloroformate, controlling the reaction temperature at 50-60° C., and reacting for 5 hours. The reaction solution was washed 3 times with 15 g of 10% hydrochloric acid, 3 times with 15 g of saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 Dry, and remove the solvent under reduced pressure to obtain the crude product, which is separated by silica gel column chromatography, and the eluent is a mixed solution of petroleum ether and ethyl acetate, petroleum ether:ethyl acetate=10:1, to obtain a white crystalline powder 4- Androstene-3β, 17β-diol bis(ethyl carbonate) 13.0 g, yield 86.7%. m.p.110-113°C.

Embodiment 3

[0017] Example 3. Dissolve 10g of 4-androstenediol in 150g of dichloromethane, N 2 protection, electromagnetic stirring, adding 30 g of triethylamine, slowly adding 20 g of ethyl chloroformate, controlling the reaction temperature at 50-60° C., and reacting for 5 hours. The reaction solution was washed 3 times with 15 g of 10% hydrochloric acid, 3 times with 15 g of saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 Dry, and remove the solvent under reduced pressure to obtain the crude product, which is separated by silica gel column chromatography, and the eluent is a mixed solution of petroleum ether and ethyl acetate, petroleum ether:ethyl acetate=10:1, to obtain a white crystalline powder 4- Androstene-3β, 17β-diol bis(ethyl carbonate) 12.0 g, yield 80%. m.p.111.5~113.5℃.

[0018] The present invention is particularly suitable for preparing novel organic compound 4-androstene-3β, 17β-diol bis(ethyl carbonate). The new organic compound has good oral activity and is...

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PUM

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Abstract

The present invention relates to a new organic compound and its preparation process. The new organic compound, 4-androstene-3 beta, 17 beta-diol bis(ethylcarbonic acid) ester, is prepared by using 4-androstene diol and ethyl chloroformate as raw material and through one-step esterification in dichloromethane solvent. The process is simple and has high yield, and the said organic compound has excellent orally taken activity and is easy to be absorbed by intestinal tract to produce long-period acting. The compound is suitable for use as nutritious healoth product for reducing fat and strengthening muscle hardness.

Description

technical field [0001] The invention relates to a new organic compound 4-androstene-3β, 17β-diol bis(ethyl carbonate) ester and a preparation method thereof, belonging to the technical field of new organic compounds and organic compound preparation. The structural formula and chemical name of the organic compound are and 4-androstene-3β, 17β-diol bis(ethyl carbonate). Background technique [0002] 4-Androstenediol is a Prosteroid (steroid precursor) compound with good protein anabolic effect. And the nature of androgen is very weak, so it is used as a nutritional health product in the United States and other countries to reduce fat, increase muscle hardness, and quickly build body. However, a prominent disadvantage of this compound is that its oral activity is too low. If it is taken as a health food in large doses, it will be troublesome and uneconomical; if it is taken with a 17α-alkyl derivative with higher oral activity, it will be potentiall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 汤杰潘朝阳杨帆蒋胜力洪镛裕陈建华
Owner EAST CHINA NORMAL UNIV