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Method for preparing progesterone

A technology for progesterone and androstenedione, which is applied in the directions of steroids and organic chemistry, can solve the problems of increased progesterone synthesis cost and labor cost, and achieves high production application and economic value, simple circuit and easy operation. Effect

Active Publication Date: 2014-01-22
ZHEJIANG SHENZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the development of the west and inland areas, the labor cost has increased, and the prices of Dieteran and turmeric are also getting higher and higher, resulting in a straight-line upward trend in the price of dienolone acetate, which also makes the synthesis of progesterone greatly increased cost

Method used

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  • Method for preparing progesterone

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] Put 30g of raw material 4AD, 30mL of methanol, 45mL of acetone cyanohydrin into the reaction vessel, raise the temperature to dissolve, add potassium carbonate aqueous solution (1.0g of potassium carbonate + 100mL), and keep the reaction at 30-50°C for about 20 hours. Cool the reaction solution to 0-10°C, keep it warm for 30 minutes, filter and flush with water, soak the filter cake in 10% dilute hydrochloric acid for 0.5 hours, filter to obtain the crude product, and refine 17-hydroxycyano-4-androsten-3-one (compound 1), the yield is about 95% (m / m); the product is a mixture of isomers.

[0035] EI MS (70eV, m / z): 313 (M + ,75%).

Embodiment 2

[0037]

[0038] Add 5g of compound 1, 25mL of pyridine, stir and add 5mL of phosphorus oxychloride, raise the temperature to 115°C, reflux for 30 minutes, TLC shows that the reaction is complete, lower the temperature below 10°C, slowly add water dropwise until it is completely dissolved, concentrate under reduced pressure, and water analysis, Filter and flush water to neutral to get wet product. Then dissolve it with dichloromethane, separate the water layer, filter, concentrate under reduced pressure to dryness, crystallize methanol, freeze, filter a small amount of ice methanol, rinse, and dry to obtain 17-cyano-4,16-androstadiene- 3-Keto (Compound 2), 3.2g. The yield is about 65% (m / m). EI MS (70eV, m / z): 295 (M + ,80%); 1 H NMR (300MHz, CDCl 3 )δ6.61(m,1H,16-H),5.71(s,1H,4-H),1.20(s,3H,19-H),0.95(s,3H,18-H); 13 C NMR (100MHz, CDCl 3 )δ199.3, 170.1, 147.3, 127.2, 124.2, 115.7, 55.3, 53.9, 48.1, 38.7, 35.6, 34.1, 33.9, 33.8, 32.8, 32.5, 31.6, 20.6, 17.2, 16.3.

Embodiment 3

[0040]

[0041] Add 5g of compound 2, 4.3mL of ethylene glycol, 3mL of triethyl orthoformate and 30mL of dichloromethane into the reaction vessel, then add the catalyst p-toluenesulfonic acid 0.29g, react at 35-45°C for 8-12 hours, and the reaction is complete Afterwards, the reaction solution was neutralized with an alkaline solution at 0-5°C, concentrated, water-analyzed, filtered, and the filter cake was washed with water until neutral recrystallization, and dried to obtain 3,3-ethylenedioxy-17-cyano-4, 4.25 g of 16-androstadiene (compound 3), the yield is about 85% (m / m). EI MS (70eV, m / z): 339 (M + ,78%); 1 H NMR (300MHz, CDCl 3 )δ 6.61(m,1H,16-H),5.34(m,1H,6-H),3.94(m,4H,-OCH 2 CH 2 O-),1.05(s,3H,19-H),0.93(s,3H,18-H).

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Abstract

The invention relates to a method for preparing progesterone. According to the method, 4-androstenedione is used as raw materials, and hydroxyl cyanation, dehydration, protection, hydrogenation and addition hydrolysis reaction are carried out in sequence, and the progesterone is obtained. The 4-androstenedione which has the price advantage is used as the raw materials, the reaction condition is easy to control, post-processing is easy, and yield is high.

Description

technical field [0001] The present invention relates to a synthesis method of chemical drugs, in particular to a method for preparing progesterone, which uses 4-androstenedione (4AD) as a raw material, and undergoes successive reactions of hydroxycyanation, dehydration, protection, hydrogenation, and addition hydrolysis Progesterone is produced. Background technique [0002] Progesterone is the most important natural progesterone. It was isolated from pregnant urine in 1934 and its structure was determined as Δ 4 -3-ketopregnane. Progesterone plays an important role in the secretion transformation of endometrium, decidualization process, maintenance of sexual cycle and maintenance of pregnancy. It is also the main component of female steroidal oral contraceptives and has very important clinical uses; Progesterone is also the precursor of corticosteroids, androgens and estrogens, which promotes the research of steroid hormone drugs. [0003] For a long time, the synthesis ...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 王友富
Owner ZHEJIANG SHENZHOU PHARMA
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