Preparation method of allylestrenol

A technology of allylestradiol and estradiol, which is applied in the field of preparation of the compound allylestradiol, can solve the problems of low yield, high cost, difficult purification and the like of intermediate 5, achieves improved quality and yield, and is suitable for technological production. , the effect of simple process

Active Publication Date: 2011-10-26
北京市科益丰生物技术发展有限公司
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Problems solved by technology

[0015] This route is relatively simple to operate, but the yield of the important intermediate 5 obtained by it is low, the purification is difficult, and the cost is high

Method used

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  • Preparation method of allylestrenol
  • Preparation method of allylestrenol
  • Preparation method of allylestrenol

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Embodiment Construction

[0040] (1) Preparation of compound ③ from estro-4-ene-3,17-dione

[0041] Add glacial acetic acid (75ml) into the reaction vessel, start stirring, put in compound ② (10g, 36.7mmol) and ethanedithiol (4.0ml, 47.6mmol), adjust the temperature to 5-10°C, add dropwise 4.5ml trifluoro Boronium diethyl ether was added dropwise for about 15 minutes, and then the reaction was kept at 5-10°C for 2.5 hours. Then slowly pour the reaction solution into an aqueous solution made of 60g NaOH dissolved in 450ml water at about -5°C, stir for about 30 minutes after the water analysis is completed, let it stand for about 1 hour, filter with suction, wash the filter cake with water until it is neutral, and drain it. , recrystallized to obtain white solid compound ③ (12.7g, 36.4mmol) with a yield of 99%, m.p=220-223°C.

[0042] (2) Preparation of compound ④

[0043] Add ethylene glycol (40ml) and triethyl orthoformate (40ml) into the reaction vessel, start stirring, put in compound ③ (10g, 28.7m...

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Abstract

The invention provides a preparation method of allylestrenol. The allylestrenol is prepared by a five-step reaction based on estr-4-ene-3,17-dione as a starting material. The method comprises the following steps: 1) carrying out dithioketal protection on 3-keto so as to obtain a compound (3); 2) carrying out dihydric alcohol ketal protection on 17-keto so as to obtain a compound (4); 3) removing 3-thioaketal through a Birch reduction reaction so as to obtain a compound (5); 4) hydrolyzing for 17-position deprotection so as to obtain a compound (6); and 5) carrying out Grignard reaction so as to obtain a target compound (1). Through a reaction route in the invention, the high-purity product is obtained in high yield and high selectivity; and operation is simple, synthesis route is short, and purification is convenient, thereby greatly reducing production cost. The method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a preparation method of the compound allylestradiol. Background technique [0002] Allylestrenol [0003] Chemical name: (17β)-17-(2-propenyl)est-4-en-17-ol [0004] (17)-17-(2-Propenyl)estr-4-en-17-ol [0005] CAS: 432-60-0 [0006] Structural formula: [0007] [0008] Allylestradiol is an oral 17-hydroxyprogesterone. Because its progesterone activity is significantly stronger than that of progesterone, it has no androgen activity, and it can increase the activity of trophoblast cells and stimulate placental function, so it can be used for threatened abortion. Especially because of hormone deficient miscarriages. Allylestradiol’s natural chemical structure makes it effective for oral administration, stable metabolism, high selectivity for progesterone receptors, no estrogen and androgen effects, can enhance the concentration and activity of oxytocin enzymes,...

Claims

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Application Information

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IPC IPC(8): C07J11/00
Inventor 郑正春何亮童志杰周江
Owner 北京市科益丰生物技术发展有限公司
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