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Preparation method of ethinylestradiol

A technology for ethinyl estradiol and estrone, which is applied in the field of drug preparation, can solve the problems of low production efficiency, difficult process control, long reaction time, etc., and achieves the effects of low reaction device requirements, improved reaction efficiency, and mild reaction conditions.

Inactive Publication Date: 2020-09-18
ZHEJIANG SHENZHOU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The method utilizes toluene azeotropic dehydration to prepare potassium acetylide, which has low production efficiency and high energy consumption, and is unfavorable for industrialized production
[0006] The traditional preparation method of ethinyl estradiol also introduces ethynyl group with Grignard reagent or lithium reagent, first prepares Grignard reagent or lithium reagent with acetylene, and then reacts with estrone to obtain ethinyl estradiol. The Grignard reagent and lithium used in this method Reagents are expensive, the reaction is long and the process is difficult to control, there are great safety hazards, and it is also not suitable for industrial production

Method used

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  • Preparation method of ethinylestradiol
  • Preparation method of ethinylestradiol
  • Preparation method of ethinylestradiol

Examples

Experimental program
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Effect test

Embodiment 1

[0023] The preparation of embodiment 1 ethinyl estradiol

[0024] Dissolve 50g of estrone in 250ml of tetrahydrofuran, add 50g of potassium tert-butoxide, control 5°C, pass through acetylene, stir the reaction, after the reaction, neutralize with 5% hydrochloric acid aqueous solution, concentrate, add water for water analysis, filter to obtain the crude product , the crude product was refined with ethanol and dried to obtain 46 g of ethinyl estradiol, the mass yield of the product was 92%, the melting point of the product was 182.0-183.5° C., and the HPLC content was 99.5%.

Embodiment 2

[0025] The preparation of embodiment 2 ethinyl estradiol

[0026] Dissolve 50g of estrone in 100ml of dimethyl sulfoxide and 800ml of toluene, add 70g of potassium isobutoxide, control the temperature at 30°C, pass through acetylene, and stir the reaction. After the reaction, neutralize with 10% sulfuric acid aqueous solution, concentrate, Water was added for water analysis and filtered to obtain a crude product, which was refined with methanol and dried to obtain 47 g of ethinyl estradiol. The mass yield of the obtained product was 94%, the melting point of the product was 182.5-183.9° C., and the HPLC content was 99.6%.

Embodiment 3

[0027] The preparation of embodiment 3 ethinyl estradiol

[0028] Dissolve 50g of estrone in 1500ml of acetone, add 250g of sodium ethoxide, control the temperature at -20°C, pass through acetylene, stir the reaction, after the reaction, neutralize with 35% acetic acid aqueous solution, concentrate, add water for water analysis, filter to obtain the crude product , the crude product was refined with acetone and dried to obtain 45.5 g of ethinyl estradiol, the mass yield of the product was 91%, the melting point of the product was 182.1-183.2°C, and the HPLC content was 99.5%.

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Abstract

The invention discloses a preparation method of ethinylestradiol, and belongs to the technical field of medicine preparation and processing. According to the method, estrone is used as an initial rawmaterial, and the ethinylestradiol is prepared through one-step ethynylation reaction. According to the method, the reaction process can be effectively shortened by improving the defects of a traditional process, reaction conditions are mild, a lithium reagent and a Grignard reagent with large potential safety hazards are avoided, and the method is high in overall conversion rate, easy and convenient to operate and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a preparation method of ethinyl estradiol. Background technique [0002] Ethinylestradiol, English name is Ethinylestradiol, chemical name is 3-hydroxy-19-nor-17α-pregna-1,3,5(10)-triene-20-yn-17-ol, is an oral Effective and powerful estrogen, supplementing estrogen deficiency, treating female hypogonadism, amenorrhea, menopausal syndrome, etc., combined with progesterone drugs, can inhibit ovulation, can be used as contraceptives, and can also treat gonadotropin deficiency. Hypogonadal amenorrhea and infertility, multi-follicular ovary infertility. [0003] The preparation method of ethinyl estradiol in "National Compendium of Raw Materials Processes" is to use potassium hydroxide, isobutanol and toluene to azeotropically dehydrate, then react with acetylene to prepare potassium acetylene, and finally react with estrone to obtain ethinyl estradiol, the reaction rou...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0096
Inventor 邵振平王荣王炳乾王洪福黄橙橙雷灵芝王友富
Owner ZHEJIANG SHENZHOU PHARMA
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