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Preparation method of progesterone

A technology of progesterone and volume, applied in the direction of steroids, organic chemistry, etc., can solve the problems of low total yield, long reaction route, large pollution, etc., and achieve the effects of small environmental pollution, simple production operation, and high success rate

Inactive Publication Date: 2020-02-11
ZHEJIANG SHENZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the limitations of the existing progesterone preparation method with long reaction route, low total yield and large pollution, and provide a new progesterone preparation method with short reaction route, less pollution and high yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Oxidation Reaction: Preparation of 20-formylpregn-4-en-3-one (2) 1

[0023] Add 25 grams of 21-hydroxy-20-methylpregn-4-en-3-one (1) and 150 milliliters of toluene into the reaction flask, stir and dissolve, then add 0.7 grams of TEMPO, 2 grams of potassium bromide, and 1.5 grams of carbonic acid Sodium hydrogen and 35 milliliters of water, 75 milliliters of mass concentrations are added dropwise and are 5% sodium hypochlorite aqueous solution, 10 ℃ of stirring reactions, after reaction is completed, add 25 milliliters of mass concentrations and be that 15% sodium thiosulfate aqueous solution quenches reaction, stand layering, The organic layer was washed with water until neutral, concentrated, analyzed by water, filtered and dried to obtain 23.5 g of 20-formylpregn-4-en-3-one (2).

Embodiment 2

[0024] Example 2 Oxidation Reaction: Preparation 2 of 20-formylpregn-4-en-3-one (2)

[0025] Add 25 grams of 21-hydroxy-20-methylpregn-4-en-3-one (1) and 150 milliliters of dichloromethane into the reaction flask, stir and dissolve, then add 0.5 grams of 4-hydroxy-TEMPO, 1.8 grams of bromine Potassium chloride, 1.5 grams of sodium bicarbonate and 40 milliliters of water, 70 milliliters of mass concentration is added dropwise and is 10% sodium hypochlorite aqueous solution, and -10 ℃ stirs reaction, after reaction is completed, add 70 milliliters of mass concentration and be that 5% sodium thiosulfate aqueous solution is quenched After the reaction, the layers were allowed to stand, and the organic layer was washed with water to neutrality, concentrated, water-analyzed, filtered, and dried to obtain 23.0 g of 20-formylpregn-4-en-3-one (2).

Embodiment 3

[0026] Example 3 Oxidation reaction: Preparation of 20-formylpregn-4-en-3-one (2) 3

[0027] Add 25 grams of 21-hydroxyl-20-methylpregn-4-en-3-one (1) and 150 milliliters of dichloroethane in the reaction flask, stir and dissolve, then add 0.8 grams of 4-hydroxyl-TEMPO, 2.0 grams of Potassium bromide, 1.8 grams of sodium bicarbonate and 45 milliliters of water are added dropwise with 75 milliliters of mass concentration of 15% sodium hypochlorite aqueous solution, and the reaction is stirred at 0°C. After the reaction is completed, adding 35 milliliters of mass concentration of 10% sodium thiosulfate aqueous solution is quenched After the reaction, the layers were allowed to stand, and the organic layer was washed with water until neutral, concentrated, water-analyzed, filtered, and dried to obtain 23.2 g of 20-formylpregn-4-en-3-one (2).

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Abstract

The invention discloses a preparation method of progesterone, and belongs to the technical field of preparation and processing of steroid hormone drugs. The preparation method comprises the steps that21-hydroxy-20-methylprogesterone-4-ene-3-ketone (1) is used as a starting material, 20-formylprogesterone-4-ene-3-ketone (2) is obtained through an oxidation reaction step, then an oxidative decarburization reaction step is performed under the action of a catalyst, and the product progesterone (3) is obtained. Compared with the prior art, the preparation method of the progesterone is shorter in reaction route and higher in yield, the adopted raw materials are low in cost and easy to obtain, less pollution is generated in the reaction process, the industrial development trend of green chemistry is met, and good social benefits and broader market prospects are achieved.

Description

technical field [0001] The invention relates to the technical field of preparation and processing of steroid hormone drugs, in particular to a preparation method of progesterone. Background technique [0002] Progesterone, also known as progesterone, is the main biologically active progesterone secreted by the corpus luteum of the ovary, the adrenal cortex and the placenta, and plays a very important role in maintaining pregnancy. Under the synergistic effect of estrogen, progesterone makes the endometrium complete the change from the proliferative phase to the secretory phase, so that the fertilized egg can be implanted stably; it promotes the relaxation of the pregnant uterine muscle and reduces the activity ability, reduces the sensitivity of the pregnant uterus, and is beneficial to the fertilized egg It grows and develops in the womb; it also has the function of immunity, directly participates in the regulation of the environment in the mother's fetus, and promotes mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 邵振平黄橙橙王荣王炳乾张宇波王友富
Owner ZHEJIANG SHENZHOU PHARMA
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