Method for preparing progesterone and derivatives thereof

A technology of derivatives and progesterone, which is applied in the field of chemical preparation, can solve the problems of restricting large-scale industrial production, high raw material costs, and long synthetic routes, and achieve the effects of short synthetic routes, high product quality, and easy monitoring

Inactive Publication Date: 2017-04-26
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The purpose of the present invention is to solve the problem of high raw material cost, long synthetic route, many steps, long production cycle, many by-products and low yield for the preparation of progesterone and its derivatives, which limit its large-scale industrial production. question

Method used

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  • Method for preparing progesterone and derivatives thereof
  • Method for preparing progesterone and derivatives thereof
  • Method for preparing progesterone and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The first step, oxidation reaction: Add PCC (20g, 1W) and dichloromethane (200ml, 10V) to the dry three-necked flask, stir to dissolve, add silica gel (30g, 1.5W), under nitrogen protection, the internal temperature is controlled at 20~25 ℃, weigh compound 1 (20g, 1W) and dissolve it in dichloromethane (100ml, 5V), transfer it to the dropping funnel, and drop it into the three-necked bottle. The temperature during the dropping process should not exceed 25°C. , kept at this temperature for 5 hours. After the reaction was completed, filter, the filter cake was washed with dichloromethane (200ml, 10V), and the filtrate was concentrated under reduced pressure until dripping without solvent to obtain oxide 2 (18.8g). The weight yield was 94%. HPLC (High Performance Liquid Chromatography, high performance liquid phase chromatography) content of 98%.

[0040] The second step, rearrangement reaction: Add oxide 2 (18.8g, 1W) and DMF (56ml, 3V) into the reaction flask, stir and ...

Embodiment 2

[0042] The first step, oxidation reaction: add PDC (30g, 1.5W) and chloroform (200ml, 15V) to the dry three-necked flask, stir to dissolve, add silica gel (30g, 1.5W), under the protection of nitrogen, the internal temperature is controlled at 0~ 10°C, weigh compound 1 (20g, 1W) and dissolve it in chloroform (100ml, 5V), transfer it to the dropping funnel, and drop it into the three-necked bottle. Afterwards, the reaction was incubated at this temperature for 6 hours. After the reaction was completed, it was filtered, and the filter cake was washed with chloroform (200ml, 10V). The filtrate was concentrated under reduced pressure until dripping without solvent to obtain oxide 2 (18.0g). The weight yield was 90%, and the HPLC content was 96%.

[0043] The second step, rearrangement reaction: Add oxide 2 (18g, 1W) and dimethylacetamide (36ml, 2V) into the reaction flask, stir and control the temperature to 20°C, add 2,2'-bipyridine (0.02g , 0.001W), copper acetate (0.02g, 0.001...

Embodiment 3

[0045]The first step, oxidation reaction: Add PCC (40g, 2W) and 1,2-dichloroethane (400ml, 20V) to a dry three-necked flask, stir to dissolve, add silica gel (30g, 1.5W), under nitrogen protection, Control the temperature at 25~30°C, weigh compound 1 (20g, 1W) and dissolve it in 1,2-dichloroethane (200ml, 10V), transfer it to the dropping funnel, and drop it into the three-necked bottle. Not more than 30°C, after the dropwise addition is completed, keep the reaction at this temperature for 1 hour. After the reaction was completed, filter, the filter cake was washed with 1,2-dichloroethane (200ml, 10V), and the filtrate was concentrated under reduced pressure until no solvent was dropped, and the weight yield of oxide 2 (18.6g) was 93%, and the HPLC content was 92%. .

[0046] The second step is the same as in Example 2.

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Abstract

The invention discloses a method for preparing progesterone and derivatives thereof. A compound 1 serves as a starting material, and through an oxidation reaction and a rearrangement reaction, the progesterone and derivatives thereof, namely, compounds 3 are obtained, wherein the reaction formula is defined in the description. By means of the method, the finished product progesterone and derivatives thereof are obtained with the total yield being 75wt% or above; the method is low in cost, environmentally friendly and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing progesterone and its derivatives. Background technique [0002] Progesterone, also known as progesterone, is a very important natural progesterone secreted by the corpus luteum of the ovary. It has a significant morphological effect on the endometrium in the body. In the late menstrual cycle, it makes the glands in the uterine mucosa grow and the uterus is congested. The intima thickens in preparation for implantation of a fertilized egg. It can also be used as a very important clinical application, mainly used for threatened abortion, habitual abortion, premenstrual syndrome, anovulatory DUB and anovulatory amenorrhea. It can be used in combination with estrogen to treat menopausal syndrome. is necessary to maintain pregnancy. [0003] The structural formula of progesterone is: [0004] [0005] Several routes about preparing progesterone in the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 陈德家戴静夏春年
Owner ZHEJIANG XIANJU PHARMA
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