A method for synthesizing 6-methylene-17α-hydroxyl-19-norpregna-4-ene-3,20-dione

A technology of norpregnantine and methylpregnantine, which is applied in the directions of steroids, organic chemistry and the like, can solve the problems of low yield and high cost, and achieve the effects of low cost and short synthesis process.

Active Publication Date: 2019-03-05
丽江映华生物药业有限公司 +1
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Problems solved by technology

This process route mainly obtains 17α-hydroxyprogesterone through the oxidation of 17(20) double bond, and the yield is low and the cost is high

Method used

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  • A method for synthesizing 6-methylene-17α-hydroxyl-19-norpregna-4-ene-3,20-dione
  • A method for synthesizing 6-methylene-17α-hydroxyl-19-norpregna-4-ene-3,20-dione

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Embodiment Construction

[0014] Below in conjunction with embodiment the present invention is further described.

[0015] The present invention uses 17α-hydroxyl-19-norpregna-4-ene-3,20-dione as raw material to synthesize 6-methylene-17α-hydroxyl-19-norpregna- 4-ene-3,20-dione, the specific route is as follows.

[0016]

[0017] 1. Preparation of 3-ethoxy-17α-hydroxyl-19-desmethylpregn-4-en-20-one

[0018] Dissolve 17α-hydroxy-19-norpregna-4-ene-3,20-dione (3g, 9.5mmol) in absolute ethanol (15mL), add p-toluenesulfonic acid monohydrate (0.07g), and Add triethyl orthoformate (2.82g, 19mmol), stir the reaction solution at 20°C for 30min, raise the temperature to 80°C and continue stirring for 30min, concentrate under reduced pressure to remove most of the solvent, add a small amount of ethyl acetate to help dissolve, add excess petroleum The ether is nearly turbid, and placed in a refrigerator at -7°C overnight, the precipitated crystals are filtered, washed with petroleum ether, and dried under re...

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Abstract

The invention provides a method for synthesizing 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone. The method comprises the steps of (1) using 17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone for preparing 3-ethyoxyl-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-20-ketone; (2) using the product in the step (1) for preparing 3-ethyoxyl-6-(N-methyl-N-phenyl) aminomethyl-17 alpha-hydroxy-19-desmethyl pregnene-4,6-diene-20-ketone; (3) using the product in the step (2) for preparing the 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone. According to the method provided by the invention, the 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone is synthesized through three-step reaction, a synthetic process is simple and short, and low in cost, and the yield achieves 55 percent or above.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing 6-methylene-17α-hydroxyl-19-norpregna-4-ene-3,20-dione. Background technique [0002] 6-methylene-17α-hydroxy-19-norpregna-4-ene-3,20-dione (structural formula 1) is an important intermediate in the synthesis of nomegestone, which is esterified with acetic anhydride Reaction and double bond displacement to obtain the fourth generation progesterone nomegestrol. [0003] [0004] Nomegestrol is a new type of high-efficiency oral progestin, which has the characteristics of good contraceptive effect, small toxic and side effects, convenient use and safety. In addition, nomegestone has a good effect on endometrial displacement syndrome (Chinese Pharrnacological Bulletin2004Nov; 20(11): 1215-7) and reversal of multidrug resistance of breast cancer cell lines (ChinaOncol.March 2002Vol24. No.2). The existing method for synthesizing nomegestrol mainly contains...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
CPCC07J7/0045
Inventor 张小元陆何林宋树勇王钱刚黄云生
Owner 丽江映华生物药业有限公司
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