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Synthesis method of drospirenone key intermediate bromide

A synthesis method and technology of intermediates, applied in steroids, organic chemistry and other directions, can solve the problems of poor selectivity, large amount of phosphorus-containing waste liquid, large amount of organic alkali, etc., and achieve convenient post-processing, high atom economy, The effect of reducing usage

Active Publication Date: 2022-05-06
台州仙琚药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the poor selectivity of the existing 3-pivaloyloxy-5β, 6β-epoxy-7-bromo-15β, 16β-dimethylene-pregnant-17-ketone synthesis method , large amount of organic

Method used

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  • Synthesis method of drospirenone key intermediate bromide
  • Synthesis method of drospirenone key intermediate bromide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Add 2.08g (5mmol) of 3-pivaloyloxy-5β,6β-epoxy-7β-hydroxyl-15β,16β-dimethylene-pregna-17-one, 0.13g (1mmol) aluminum chloride, 0.65g (7.5mmol) lithium bromide and 15g silica gel, then add stainless steel balls with a diameter of 8mm and place them in the ball mill, set the operating frequency of the ball mill to 12Hz, and stop the mechanical grinding after 0.5h. The entire reaction mixture was transferred from the grinding tank to a beaker, added 15 mL of dichloromethane to soak for 1 hour, filtered, and the filtrate was concentrated to dryness, and then recrystallized by adding 33 mL of a mixed solvent of ethanol and water (volume ratio: 10:1) to obtain 2.03 g of white solid 3-pivaloyloxy-5β,6β-epoxy-7-bromo-15β,16β-dimethylene-pregna-17-one, yield 85%.

[0027] After testing, the specific characteristics of the product are as follows:

[0028] Melting point: 198-201℃, 1 H NMR (600MHz, CDCl 3 )δ4.86-4.75(m,1H),4.74-4.71(m,1H),3.43(d,1H,J=2.4Hz),2.15-2.03(m...

Embodiment 2

[0030] According to the method and steps of Example 1, the only difference is that in step (1), the molar ratio of raw material and Lewis acid is adjusted to 1:0.5, and the yield is 88%.

Embodiment 3

[0032] According to the method and steps of Example 1, the only difference is that in step (1), the molar ratio of the raw material and the brominating reagent is adjusted to 1:1, and the yield is 74%.

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Abstract

The invention belongs to the technical field of pharmaceutical chemical industry, discloses a synthesis method of a drospirenone key intermediate bromide, and particularly relates to a synthesis method of 3-pivaloyloxy-5beta, 6beta-epoxy-7-bromo-15beta, 16beta-dimethylene-pregna-17-ketone, the preparation method comprises the following steps: (1) adding 3-pivaloyloxy-5beta, 6beta-epoxy-7-bromo-15beta, 16beta-dimethylene-pregna-17-ketone into a ball milling tank, and stirring at the temperature of 50-60 DEG C for 2-3 hours; the preparation method comprises the following steps: carrying out a reaction on 6 beta, 6 beta-epoxy-7 beta-hydroxy-15 beta, 16 beta-dimethylene-pregna-17-ketone, lewis acid, a bromination reagent and silica gel at a certain mechanical grinding frequency; and (2) carrying out post-treatment on the reaction liquid, so as to obtain 3-pivaloyloxy-5beta, 6beta-epoxy-7-bromine-15beta, 16beta-dimethylene-pregna-17-ketone as a key intermediate of drospirenone, which is a brominated substance. The preparation method disclosed by the invention has the advantages of high yield, good selectivity, low cost, less three wastes and the like, and is a green chemical synthesis method with relatively good popularization and application prospects.

Description

technical field [0001] The present invention relates to the technical field of medicine and chemical industry, in particular to a key intermediate bromide of drospirenone 3-pivaloyloxy-5β,6β-epoxy-7-bromo-15β,16β-dimethylene-pregna Synthetic method of -17-ketone. Background technique [0002] 3-pivaloyloxy-5β,6β-epoxy-7-bromo-15β,16β-dimethylene-pregna-17-one is a key intermediate in the synthesis of drospirenone. Drospirenone is a new-generation progestin with high efficiency, low toxicity and good safety, and has good natural progesterone activity. In clinical practice, drospirenone is usually combined with ethinyl estradiol to form a compound estrogen and progestin preparation, which is commonly used as an oral contraceptive for women. [0003] Currently, 3-pivaloyloxy-5β,6β-epoxy-7-bromo-15β,16β-dimethylene-pregna-17-one is synthesized by using 3-pivaloyloxy-5β, 6β-epoxy-7β-hydroxy-15β,16β-dimethylene-pregn-17-one was used as starting material, catalyzed bromination b...

Claims

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Application Information

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IPC IPC(8): C07J71/00
CPCC07J71/001Y02P20/55
Inventor 金旦妮叶有志林建东
Owner 台州仙琚药业有限公司
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