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Method for preparing 19-demethyl-4-androstenedione

A technology of androstenedione and ketal, which is applied in the field of chemical preparation, can solve the problems of high price and high production cost, and achieve the effects of less by-products, increased yield, and high yield

Active Publication Date: 2014-05-07
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When someone replaced dimethyl carbonate, it was found that N,N-dimethylformamide was used as solvent and 1,1,3,3-tetramethylguanidine was used as base, and the yield was about 96%, but 1,1, 3,3-Tetramethylguanidine is expensive and expensive to produce

Method used

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  • Method for preparing 19-demethyl-4-androstenedione
  • Method for preparing 19-demethyl-4-androstenedione
  • Method for preparing 19-demethyl-4-androstenedione

Examples

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Effect test

Embodiment 1

[0070] In the first step, add 10g of estrone and 15g of potassium carbonate into a 250ml reaction bottle, first add 100ml of solvent N,N-dimethylformamide at room temperature, then add 50ml of dimethyl carbonate, and react at 130°C for 16 hours After the reaction is completed, pour it into ice water and stir for one hour, filter, wash with water, and dry under reduced pressure at 60°C to obtain etherified compound with a yield of 104% and an HPLC content of 98%;

[0071] In the second step, add 20ml of ethylene glycol, 25ml of triethyl orthoformate, 0.2ml of boron trifluoride ether into a dry 250ml reaction bottle, stir at 25°C for 15 minutes, then add 10g of ether compound, 40ml of dichloromethane, 25 Ketal reaction at ℃ for 5 hours; TLC (thin layer chromatography) detected no raw material point, added triethylamine, stirred for 10 minutes; concentrated under reduced pressure until no distillate was evaporated, poured into ice water and stirred for one hour, filtered, washed w...

Embodiment 2

[0075] In the first step, add 10g of estrone and 20g of potassium carbonate to a 250ml reaction bottle, first add 100ml of solvent N,N-dimethylacetamide at room temperature, then add 50ml of dimethyl carbonate, and react at 100°C for 16 hours After the reaction is completed, pour into ice water and stir for one hour, filter, wash with water, and dry under reduced pressure at 60° C. to obtain an ether compound with a yield of 103% and an HPLC content of 86%.

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Abstract

The invention discloses a method for preparing 19-demthyl-4-androstenedione, which comprises the steps of: based on estrone as a raw material, sequentially carrying out etherealization reaction, ketalation, Birch reducing reaction and hydrolysis reaction to obtain19-demethyl-4-androstenedione, wherein the reaction formula is shown in the specification. According to the method provided by the invention, the traditional phenolic group methyl etherealization process is improved, methyl carbonate replaces traditional high-toxicity carcinogenic etherealization reagents dimethyl sulfate and iodomethane, and inexpensive potassium carbonate is used as a base, so that the production cost is lowered, the method is environment-friendly, the yield is high, and the method is suitable for scaled industrial production.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing 19-nor-4-androstenedione. Background technique [0002] 19-nor-4-androstenedione is a very important pharmaceutical intermediate, which can be used to synthesize norethindrone, nandrolone phenylpropionate and other drugs. Norethindrone is used for dysfunctional uterine bleeding, dysmenorrhea, irregular menstruation, endometriosis and infertility; nandrolone phenylpropionate is used for malnutrition, recovery after surgery and chronic wasting disease. [0003] The structural formula of 19-nor-4-androstenedione is: [0004] [0005] In the prior art, 19-nor-4-androstenedione is mainly prepared by decarboxylation reaction, and the "National Compilation of Raw Materials Processes" includes two commonly used methods of acidic decarboxylation and alkaline decarboxylation, that is, using chromic acid- Sulfuric acid is used as an oxidant to convert 4-androst...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J1/00
Inventor 戴静方伟明
Owner ZHEJIANG XIANJU PHARMA
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