Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of allylestrenol
  • Preparation method of allylestrenol
  • Preparation method of allylestrenol

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com