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Method for preparing 7 alpha-bromo-sterides

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

Inactive Publication Date: 2012-05-02
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-hydroxy-15β,16β-methylene-androst-17-one into the reaction flask and add 20ml of dichloromethane 20ml of pyridine, and pyridine, keep the temperature at 25℃, add 11.8g of triphenylphosphine after dissolving, dilute 1.3ml of liquid bromine with 5ml of dichloromethane and add it dropwise to the reaction flask within 1 hour. The reaction is stirred for about 2 hours.

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

[0036] After the reaction, water was added to terminate the reaction, the organic phase was extracted and separated, and the organic phase was washed twice with water. Combine all the aqueous phases and back extract with dichloromethane. Combine all organic phases and dry with anhydrous sodium sulfate for 30 minutes. Concentrate to dryness, add methanol twice, and concentrate to remove residual dichloromethane. Add methanol to the residue for beating. ...

Embodiment 2

[0038] Under the protection of argon, put 10g of 3β-pivaloyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-androst-17-one into the reaction flask and add 20ml of dichloromethane 20ml of pyridine, and pyridine, the temperature is kept at 25℃, after dissolving, add 8.2g of triphenylphosphine, dilute 1.5ml of bromine with 5ml of dichloromethane and add it dropwise to the reaction flask within 1 hour. The reaction is stirred for about 4 hours.

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

[0040] After drying, the product 3β-pivaloyloxy-5,6β-epoxy-7α-bromo-15β,16β-methylene-androst-17-one is 9.6g, the yield is 84%, and the purity by HPLC is 92 %.

Embodiment 3

[0042] Under the protection of argon, put 10g of 3β-pivaloyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-androst-17-one into the reaction flask, and add 25ml of dichloromethane , And pyridine 25ml, keep the temperature at 20℃, add 14.5g of triphenylphosphine after dissolving, dilute 2.0ml of bromine with 6ml of dichloromethane, add dropwise to the reaction flask within 1 hour, after dripping The reaction is stirred for about 2 hours.

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

[0044] After drying, the product 3β-pivaloyloxy-5,6β-epoxy-7α-bromo-15β,16β-methylene-androst-17-one 8.1g, the yield is 70%, and the purity by HPLC is 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 fromreaction 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 present invention relates to a method for preparing 7α-bromo steroids, in particular to a method for stereoselective synthesis of 7α-bromo steroids. Background technique [0002] 7α-bromo steroid is a key intermediate for the synthesis of a new steroidal progestin trespirenone. US4435327 describes a synthetic method of 7α-halogenated steroids: [0003] The compound of formula VII is catalyzed by triphenylphosphorus, and its 7β-hydroxyl group is stereoselectively chlorinated with carbon tetrachloride as a chlorination reagent to obtain 7α-chloride (compound of formula VIII). The specific reaction formula is as follows: [0004] [0005] However, the above synthesis method has some defects. The chlorination reagent used is carbon tetrachloride, and the amount used is large (as part of the solvent and as a reaction reagent), and carbon tetrachloride has a strong destructive effect on the ozone layer. With the strengthening of environmental protection work, t...

Claims

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Application Information

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