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Method for preparing 19-nor-5(10)-androstenone compound

A technology of androstenone and compounds, which is applied in the field of chemical preparation, can solve problems such as singleness, and achieve the effects of simple operation steps, low cost of raw materials, and high reaction conversion rate

Active Publication Date: 2016-02-03
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-nor-5(10)-androstenone compound
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  • Method for preparing 19-nor-5(10)-androstenone 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07J1/00C07J21/00
CPCY02P20/55
Inventor 戴静李连武
Owner ZHEJIANG XIANJU PHARMA
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