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Method for preparing 19-Norandrost-5(10)-ene-3,17-dione compound

A technology for androstenone and compounds is applied in the field of chemical preparation, can solve problems such as singleness, and achieves the effects of simple operation steps, cheap and easy-to-obtain raw materials, and short process routes

Active Publication Date: 2014-02-26
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the current literature reports, the Birch reduction product with a ketal protecting group at the 17th position is hydrolyzed, and only a single 19-nor-5(10)-androstenedione can be obtained without reaction conditions

Method used

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  • Method for preparing 19-Norandrost-5(10)-ene-3,17-dione compound
  • Method for preparing 19-Norandrost-5(10)-ene-3,17-dione compound
  • Method for preparing 19-Norandrost-5(10)-ene-3,17-dione compound

Examples

Experimental program
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Effect test

Embodiment 1

[0073] 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 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 99% and an HPLC content of 98% (240nm);

[0074] 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, and stir at 25°C for 15 minutes; then add 10g of ether compound, 40ml of dichloromethane, React for 5 hours at ℃; TLC (thin layer chromatography) detects no raw material point, add triethylamine, stir for 10 minutes; concentrate under reduced pressure until no fraction is distilled, pour into ice water and stir for one hour, filter, wash with water, and store at ...

Embodiment 2

[0081] Preparation of 19-nor-5(10)-androstenedione: in the fourth step, add 10 g of the Birch reduction product, 160 ml of acetone, 40 ml of water, and 5 g of malonic acid into a 500 mL reaction flask, and react at 20 ° C for 5 hours. TLC detects that there is no raw material point, cool to 0 degrees, add 20% aqueous sodium hydroxide solution to adjust the pH value to neutral; recover the solvent under reduced pressure, pour it into ice water and stir for one hour, filter, wash with water, and dry under reduced pressure at 60°C to obtain 19-nor-5(10)-androstenedione, yield 95%, HPLC content 90% (202nm).

Embodiment 3

[0083] Preparation of 19-nor-5(10)-androstenedione: in the fourth step, add 10 g of the Birch reduction product, 160 ml of acetone, 40 ml of water, 20 g of malonic acid into a 500 mL reaction flask, and react at 20 ° C for 2 hours. TLC detected no raw material point, cooled to 0 degrees, added 20% sodium hydroxide aqueous solution to adjust the pH value to neutral; recovered the solvent under reduced pressure, poured into ice water and stirred for one hour, filtered, washed with water, and dried under reduced pressure at 60°C to obtain 19-nor-5(10)-androstenedione, yield 95%, HPLC content 92% (202nm).

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Abstract

The invention discloses a method for preparing a 19-Norandrost-5(10)-ene-3,17-dione compound. The method comprises the steps of by taking estrone as an ingredient, firstly sequentially performing etherification reaction, ketal protection reaction and birch reduction reaction to obtain a birch reduction product; then by taking lower fatty acid as a catalyst, performing selective hydrolysis reaction on the birch reduction product to produce the 19-Norandrost-5(10)-ene-3,17-dione compound. According to the method, the hydrolysis technology of the birch reduction product containing 17-bit ketal protecting group is optimized and improved, and the single 19-Norandrost-5(10)-ene-3,17-dione with high yield and high selectivity can be obtained through selective hydrolysis reaction by taking binary fatty acid as an acid catalyst for the first time; in addition, the fact that the 17-bit ketal protecting derivatives of the single 19-Norandrost-5(10)-ene-3,17-dione compound can be obtained by taking lower unitary fatty acid as a catalyst is found for the first time.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing 19-nor-5(10)-androstenone compound. Background technique [0002] 19-nor-5(10)-androstenedione is a very important pharmaceutical intermediate with a great market prospect and can be used to synthesize mifepristone and other drugs. Mifepristone is a newer antiprogestin that can also be used to treat glaucoma. The structural formulas of 19-nor-5(10)-androstenedione and its 17-position ketal protected derivatives are: [0003] [0004] At present, 19-nor-5(10)-androstenedione is mainly prepared by alkali removal process, using acetic acid pregnant dienolone as the starting material, and through nine steps of reaction, it is converted into 4- Androstene-19-methanol-3,17-dione, followed by conversion of 4-androstene-19-methanol-3,17-dione to 4-androstene-19 using chromic-sulfuric acid as oxidizing agent -Carboxyl-3,17-dione, the carboxyl is heated in py...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07J21/00
CPCY02P20/55
Inventor 戴静李连武
Owner ZHEJIANG XIANJU PHARMA
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