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Synthesis method of 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one

A technology of tetrahydropyrrolyl androstane and acetoxyandrostane is applied in the field of preparation of 16β-tetrahydropyrrolyl androst-2α-epoxy-17-one, and can solve the problems of poor selectivity, difficult separation of impurities and waste liquid volume and the like , to achieve the effect of easy operation, reducing the amount of three wastes, and reducing the use of organic solvents

Active Publication Date: 2018-12-21
台州仙琚药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the defects of the existing 16β-tetrahydropyrrolylandrost-2α-epoxy-17-one synthesis method, such as poor selectivity, difficult separation of impurities and large amount of waste liquid, and provide a method with high yield , less environmental pollution, a simple and efficient new method for the synthesis of 16β-tetrahydropyrrolylandrost-2α-epoxy-17-one

Method used

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  • Synthesis method of 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one
  • Synthesis method of 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one
  • Synthesis method of 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one

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Experimental program
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Effect test

Embodiment 1

[0029] Add 3.46g (10mmol) 17-acetoxyandrosta-2α, 16α-diepoxide, 6g (50mmol) pyrrolidine and 17.3g silica gel to the ball mill jar, set the operating frequency of the ball mill to 15Hz, and stop the mechanical grinding after 20 minutes . The entire reaction mixture was transferred from the grinding jar to a 50 mL beaker, and 20 mL of dichloromethane was added to soak for 1 hour. After filtering and concentrating the filtrate to dryness, add a mixed solvent of methanol and water (10:1) for recrystallization to obtain 3.21 g of 16β-tetrahydropyrrolylandrost-2α-epoxy-17-one as a white solid, with a yield of 90% .

[0030] After testing, the specific characteristics of the product are as follows:

[0031] Melting point: 167.2-168.9℃, 1 H NMR (400MHz, CDCl 3 )δ3.18-3.12(m,2H),2.94-2.90(m,1H),2.78-2.72(m,2H),2.62-2.60(m,2H),2.17-2.08(m,1H),1.96- 1.91(m,2H),1.85-1.71(m,5H),1.67-0.95(m,13H),0.91(s,3H),0.80(s,3H),0.75-0.68(m,1H). 13 C NMR (100MHz, CDCl 3 ) 218.7, 69.1, 54.0, 52.3...

Embodiment 2

[0033] According to the method and steps of Example 1, the only difference is that in step (1), the molar ratio of 17-acetoxyandrost-2α,16α-diepoxide to pyrrolidine was adjusted to 1:3, and the yield was 78%.

Embodiment 3

[0035] According to the method and steps of Example 1, the only difference is that in step (1), the molar ratio of 17-acetoxyandrost-2α,16α-diepoxide to pyrrolidine was adjusted to 1:8, and the yield was 94%.

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Abstract

The invention relates to the technical field of medicines and chemical industry, discloses a preparation method of an important intermediate of rocuronium bromide, namely 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one. The preparation method comprises the following steps: (1), in a ball milling tank, adding 17-acetoxy androstan-2alpha,16alpha-bisepoxide, pyrrolidine and silica gel, and reacting at a certain mechanical grinding frequency; and (2), post-treating a reaction mixture, and recrystallizing to obtain the 16beta-tetrahydropyrrolyl androstan-2alpha-epoxy-17-one. The preparationmethod has the advantages of high reaction yield, short time, high selectivity, simple and convenient operation, less pollution and the like, and is an environment-friendly chemical synthesis methodwith relatively good popularization and application prospects.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a preparation method of 16β-tetrahydropyrrolylandrost-2α-epoxy-17-one. Background technique [0002] 16β-tetrahydropyrrolylandrost-2α-epoxy-17-one is an important intermediate in the synthesis of rocuronium bromide. Rocuronium bromide is a new type of non-depolarizing sterol muscle relaxant, which has the advantages of fast onset of action, no accumulation in the body, no release of histamine, weak inhibitory effect on the cardiovascular system and no allergic reaction. New anesthetic alternatives to succinylcholine. Clinically, rocuronium bromide is widely used in brain surgery, emergency eye surgery and anesthesia for patients with renal insufficiency. [0003] Prior to the present invention, the existing technology used 17-acetoxyandrosta-2α, 16α-diepoxide as a raw material to prepare 16β-tetrahydropyrrolylandrogen through hydrolysis under alkaline con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCC07J71/001
Inventor 顾光志金炜华潘建洪陈凯
Owner 台州仙琚药业有限公司
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