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Method for preparing 7 alpha-bromo-sterides

A steroidal compound, brominated technology, applied in the field of preparation of 7α-bromosteroidal compound, can solve the problems of improvement and large amount of use, and achieve the effects of simple operation, low production cost, and environmentally friendly process

Inactive Publication Date: 2009-01-14
JIANGSU CHUANGUO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But there are some defectives in the above-mentioned synthetic method, and used chlorinated reagent is carbon tetrachloride, and the amount of using is very big (not only as part solvent but also as reaction reagent), and carbon tetrachloride has stronger destructiveness to ozone layer , with the strengthening of environmental protection work, the use of this reagent will be gradually limited, so it is urgent and meaningful work to find alternative halogenated reagents
The yield of this step reaction US4435327 report also only has 79%, waits to improve

Method used

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  • Method for preparing 7 alpha-bromo-sterides
  • Method for preparing 7 alpha-bromo-sterides
  • Method for preparing 7 alpha-bromo-sterides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Under the protection of argon, put 10g of 3β-pivaloyloxy-5,6β-epoxy-7β-hydroxyl-15β,16β-methylene-androst-17-one into the reaction flask, add dichloromethane 20ml, and 20ml pyridine, keep the temperature at 25°C, add 11.8g triphenylphosphine after it dissolves, dilute 1.3ml liquid bromine with 5ml dichloromethane, drop it into the reaction flask within 1 hour, and drop it off The reaction was then stirred for about 2 hours.

[0035] The reaction was followed by TLC (developing solvent: cyclohexane: ethyl acetate = 1:4).

[0036] After the reaction was completed, water was added to terminate the reaction, the organic phase was extracted and separated, and the organic phase was washed twice with water. All aqueous phases were combined and back extracted with dichloromethane. All organic phases were combined and dried over anhydrous sodium sulfate for 30 minutes. Concentrate to dryness, add methanol twice, and concentrate again to take away residual dichloromethane. Me...

Embodiment 2

[0038] Under the protection of argon, put 10g of 3β-pivaloyloxy-5,6β-epoxy-7β-hydroxyl-15β,16β-methylene-androst-17-one into the reaction flask, add dichloromethane 20ml, and 20ml pyridine, keep the temperature at 25°C, add 8.2g triphenylphosphine after the solution is clear, dilute 1.5ml liquid bromine with 5ml dichloromethane, drop it into the reaction flask within 1 hour, drop it off The reaction was then stirred for about 4 hours.

[0039] Post-reaction treatment is the same as in Example 1.

[0040] The product 3β-pivaloyloxy-5,6β-epoxy-7α-bromo-15β,16β-methylene-androst-17-one was dried to obtain 9.6g, with a yield of 84%, and a purity of 92% by HPLC. %.

Embodiment 3

[0042] Under the protection of argon, put 10g of 3β-pivaloyloxy-5,6β-epoxy-7β-hydroxyl-15β,16β-methylene-androst-17-one into the reaction flask, add dichloromethane 25ml, and 25ml of pyridine, keep the temperature at 20°C, add 14.5g of triphenylphosphine after the solution is clear, dilute 2.0ml of liquid bromine with 6ml of dichloromethane, drop it into the reaction flask within 1 hour, and drop it off The reaction was then stirred for about 2 hours.

[0043] Post-reaction treatment is the same as in Example 1.

[0044] The product 3β-pivaloyloxy-5,6β-epoxy-7α-bromo-15β, 16β-methylene-androst-17-one 8.1g was obtained by drying, the yield was 70%, and the purity by HPLC was 90%. %.

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Abstract

The invention discloses a method for preparing a 7 Alpha-bromo steroid compound, comprising the following steps that: in the presence of a catalyst, a bromo reagent is in contact with a steroid compound having 7 Beta-oxhydryl to implement the stereoscopic selective bromation to the steroid compound having 7 Beta-oxhydryl, then the corresponding 7 Alpha-bromo steroid compound can be collected from reaction products. The method has advantages of simple operation, environment-friendly process, maximum 99 percent yield, low production costs and rather high industrialized production value.

Description

technical field [0001] The invention relates to a method for preparing 7α-bromosteroid compounds, in particular to a method for stereoselectively synthesizing 7α-bromosteroid compounds. Background technique [0002] 7α-Bromosteroid compound is a key intermediate in the synthesis of a new type of steroidal progesterone drospirenone. US4435327 describes a synthetic method of 7α-halogenated steroids: [0003] The compound of formula VII is catalyzed by triphenylphosphine, and its 7β-hydroxyl group is stereoselectively chlorinated with carbon tetrachloride as a chlorinating agent to obtain 7α-chlorinated product (compound of formula VIII). The specific reaction formula is as follows: [0004] [0005] But there are some defectives in the above-mentioned synthetic method, and used chlorinated reagent is carbon tetrachloride, and the amount of using is very big (not only as part solvent but also as reaction reagent), and carbon tetrachloride has stronger destructiveness to ozo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
Inventor 李金亮赵楠
Owner JIANGSU CHUANGUO PHARMA CO LTD
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