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Method for preparing progesterone

A technology for progesterone and intermediates, which is applied in the field of preparing progesterone, can solve the problems of operator poisoning and low yield, and achieves the effects of simple operation, good yield and favorable industrial production.

Inactive Publication Date: 2017-07-07
ZHEJIANG SHENZHOU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] It involves the highly toxic reagent acetone cyanohydrin, which is easy to poison the operator, and the yield of the method is not high

Method used

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  • Method for preparing progesterone
  • Method for preparing progesterone
  • Method for preparing progesterone

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Embodiment 1

[0039]

[0040] Diketone (20g, 0.07mol), 30L anhydrous methanol, stir, add trimethyl orthoformate (13ml, 0.12mol), stir, add 0.3kg p-toluenesulfonate, continue stirring, heat up to 35-40°C , stirred for 2 hours, added 1 mL of triethylamine, and stirred for about 1 hour. After filtration and drying, Intermediate 1 was obtained as a white solid with a yield of 95%. Melting point: 166-168°C; 1H NMR (300MHz, CDCl3) δ5.28(d, J=4.3Hz, 1H), 5.17(s, 1H), 3.55(s, 3H), 1.19(s, 3H), 0.93 (s, 3H); EI MS (70eV, m / z): 300 (M+), 285 (72%).

[0041]

[0042] Dissolve TosMIC (11.7g, 60mmol) in 150mL of dry THF, cool to -40°C, add tBuOK (8.4g, 75mmol), and react for 15 minutes, then add intermediate 1 (15.7g, 50mmol) in THF 100mL , heated up to -40 to -35°C for 2.5 hours, added phosphorous acid (6.15g, 75mmol), reacted for 15 minutes, then added triethylamine (75ml, 540mmol), phosphorus oxychloride (10ml, 110mmol), After raising the temperature to 0° C. and reacting for 1 hour, pour 2 ...

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Abstract

The invention discloses a brand-new process route for preparing progesterone. The route adopts a cheaper and easier-to-obtain starting material 4-androstenedione (4AD), each step has better reaction independence, simple circuit and easy operation. The method is suitable for industrialized production, and has good yield, and the accumulative yield of 5 steps is above 55%, even reaching 60%. In the current situation where the price of dienolone acetate, a traditional raw material, is skyrocketing, the success of this process route will have extremely high production application and economic value. More importantly, this method avoids the dramatic Toxic reagent - acetone cyanohydrin, which is economical and environmentally friendly, and is conducive to industrial production.

Description

technical field [0001] The present invention relates to a method for preparing pharmaceutical products, especially a method for preparing progesterone. The method uses 4-androstenedione (4AD) as a raw material, and undergoes etherification, addition, reduction, methylation, and hydrolysis reactions in sequence Progesterone is produced. Background technique [0002] Progesterone (Progesterone) is the most important natural progesterone, which was isolated from pregnant urine in 1934, and its structure was determined as Δ4-3-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 synt...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 王友富王荣王炳乾邵振平雷灵芝黄橙橙王瑞陈克纲应杨波
Owner ZHEJIANG SHENZHOU PHARMA
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