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Progesterone preparation method

A progesterone and product technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of unavailable raw materials, low yield, high progesterone price, etc., and achieve low price, high yield and low cost Effect

Inactive Publication Date: 2014-10-15
赵云现
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main defect of the synthetic method of above-mentioned progesterone is: raw material is difficult to obtain, and yield is low, about 80%~85%
As a result, the price of progesterone remains high

Method used

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Examples

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preparation example Construction

[0027] The embodiment of the present invention discloses a preparation method of progesterone, the method comprises the following steps:

[0028] a), under strong alkali conditions, 3-ethoxy-androst-3,5-dien-17-one and p-toluenesulfonylmethyl isonitrile react in an organic solvent to obtain formula (II) structure first intermediate product;

[0029]

[0030] b), the first intermediate product reacts with the Grignard reagent to obtain the second intermediate product of the formula (III) structure;

[0031]

[0032] c), the second intermediate product is hydrolyzed to obtain progesterone.

[0033] The preparation method of progesterone provided by the embodiment of the present invention is based on 3-ethoxyandrost-3,5-dien-17-one, which is relatively low in cost and easy to obtain in the market, as a raw material. First, the 17-keto group of the raw material One-step conversion to 17β-cyano group (step a above), then conversion of 17β-cyano group to 17β-acetyl group (st...

Embodiment 1

[0054] Example 1 Preparation of the first intermediate

[0055] Under the protection of nitrogen flow, 25g 3-ethoxy androst-3,5-dien-17-one and 45g potassium tert-butoxide were added to 1L ethylene glycol dimethyl ether and 300ml tert-butanol, and cooled to -5°C, add dropwise a solution made of 23.43g p-toluenesulfonylmethyl isonitrile and 140ml ethylene glycol dimethyl ether, after the dropwise addition is completed, return the temperature to room temperature, stir for 3h, and pour half-saturated chlorine In the sodium chloride aqueous solution, precipitates were precipitated, filtered, washed with water, and dried under reduced pressure to obtain 23.8 g of white crystals with a yield of 92%.

[0056] The proton nuclear magnetic resonance spectrum of product is as follows:

[0057] 1 H-NMR(CDCl3) 0.95(s, 3H, 18-CH 3 )

[0058] 1.20(s, 3H, 19-CH 3 )

[0059] 5.71 (s, 1H, 4-H)

[0060] It can be seen that the first intermediate product prepa...

Embodiment 2

[0062] Embodiment two prepares the first intermediate

[0063] Under the protection of nitrogen flow, 25g 3-ethoxy androst-3,5-dien-17-one and 45g potassium tert-butoxide were added to 1L ethylene glycol dimethyl ether and 300ml tert-butanol, and cooled to -5°C, add dropwise a solution composed of 22g p-toluenesulfonylmethyl isonitrile and 140ml ethylene glycol dimethyl ether, after the dropwise addition is complete, return the temperature to room temperature, stir for 3h, pour into half-saturated chlorinated In the aqueous sodium solution, precipitates were precipitated, filtered, washed with water, and dried under reduced pressure to obtain 23.3 g of white crystals with a yield of 90%. The proton nuclear magnetic resonance spectrum of product is as follows:

[0064] 1 H-NMR(CDCl3) 0.95(s, 3H, 18-CH 3 )

[0065] 1.20(s, 3H, 19-CH 3 )

[0066] 5.71 (s, 1H, 4-H)

[0067] It can be known that the first intermediate product prepared in this ex...

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Abstract

The invention discloses a progesterone preparation method which includes the following steps that a) 3-ethyoxyl-androstane-3, 5-diene-17-ketone and tosylmethyl isocyanide react in an organic solvent under the condition of strong alkali to obtain a first intermediate product of a structure of a formula (II); b) the first intermediate product reacts with a Grignard reagent to obtain a second intermediate product of a structure of a formula (III); c) the second intermediate product is hydrolyzed to obtain progesterone. The progesterone preparation method has the advantage of being low in cost and high in yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of progesterone. Background technique [0002] Progesterone (Progesterone) is also called progesterone, and its structure is shown in formula (I). Progesterone is an important progesterone, which continues to promote the development of endometrium, gland growth and branching in the late menstrual period, uterine congestion, and changes the endometrium from the proliferative phase to the secretory phase, preparing for the safe implantation of fertilized eggs into the endometrium , progesterone can also feedback the inhibition of pituitary hormone secretion, thereby inhibiting the ovulation process of the ovary. Progesterone has very important clinical uses, such as: for threatened abortion, habitual abortion, amenorrhea or reactive diagnosis of amenorrhea causes; as the main component of female steroidal oral contraceptives; as corticosteroids, andr...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 赵云现李超余伟方明山
Owner 赵云现
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