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Method for preparing 19-desmethyl-4-androstene-3,17-diketone by using one-pot method

A technology of androstene and diketone, which is applied in the field of chemical preparation, can solve the problems of long production cycle, complicated operation and high cost, and achieve the effects of high product quality, simple operation and short synthetic route

Inactive Publication Date: 2018-02-23
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The purpose of the present invention is to solve the technical problems of high cost, low yield, complicated operation and long production cycle of the current process route for preparing 19-nor-4-androstene-3,17-dione, so as to reduce acid deintermediation The overall cost, increase the yield, simplify the operation, shorten the production cycle, making it more competitive in the market

Method used

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  • Method for preparing 19-desmethyl-4-androstene-3,17-diketone by using one-pot method
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  • Method for preparing 19-desmethyl-4-androstene-3,17-diketone by using one-pot method

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Experimental program
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Effect test

Embodiment 1

[0035] The first step, hydrogenation reaction: add compound 1 (75g, 1W) and absolute ethanol (375ml, 5V) to the reaction flask, stir, add Pd / C (7.5g, 0.1W) under nitrogen protection, replace nitrogen with hydrogen, and The temperature was controlled at 50~55°C, and the reaction was kept at this temperature for 6 hours. When there was no raw material point detected by TLC, filter, the filter cake was washed with ethanol (220ml, 2V), and the filtrate was evaporated to dryness at 50°C under reduced pressure to obtain the hydrogenated product 2;

[0036] The second step, condensation reaction: add phosphoric acid (90g, 0.8W) to the hydride 2, under the protection of nitrogen, stir and raise the temperature, the internal temperature is controlled at 75~80°C, keep the reaction at this temperature for 5 hours, TLC detects no raw material point Add drinking water (500ml, 6.67V) for water analysis, lower the temperature to 5~10°C, keep stirring for 2 hours, filter, wash the filter cake ...

Embodiment 2

[0038] The first step, hydrogenation reaction: add compound 1 (100g, 1W) and benzene (300ml, 3V) into the reaction flask, stir, add palladium carbon (1g, 0.5W) under the protection of nitrogen, replace the nitrogen with hydrogen, and control the internal temperature at 20°C , keep the reaction at this temperature for 15 hours, when there is no raw material point detected by TLC, filter, the filter cake is washed with benzene (400ml, 4V), and the filtrate is evaporated to dryness at 65°C under reduced pressure to obtain the hydrogenated product 2;

[0039] The second step, condensation reaction: add phosphoric acid (50g, 0.5W) to the hydrogenation product 2, under the protection of nitrogen, the internal temperature is controlled at 20°C, and the reaction is kept at this temperature for 24 hours. When there is no raw material point detected by TLC, drinking water is added (10000ml, 100V) water analysis, lower the temperature to 5~10°C, keep stirring for 2 hours, filter, wash the...

Embodiment 3

[0041] The first step, hydrogenation reaction: add compound 1 (224g, 1W) and methanol (672ml, 3V) into the reaction flask, stir, add active nickel (112g, 0.5W) under the protection of nitrogen, replace the nitrogen with hydrogen, and control the internal temperature at 80 ℃, keep the reaction at this temperature for 2 hours, when there is no raw material point detected by TLC, filter, the filter cake is washed with methanol (224ml, 1V), and the filtrate is evaporated to dryness at 65℃ under reduced pressure to obtain the hydrogenated product 2;

[0042] The second step, condensation reaction: add phosphoric acid (2240g, 10W) ​​to the hydrogenation product 2, under the protection of nitrogen, stir and raise the temperature, control the internal temperature at 95°C, keep the reaction at this temperature for 3 hours, when there is no raw material point detected by TLC, add Drinking water (2240ml, 10V) water analysis, cooling to 5~10°C, heat preservation and stirring for 2 hours, f...

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Abstract

The invention discloses a method for preparing 19-desmethyl-4-androstene-3,17-diketone by using a one-pot method. The method for preparing 19-desmethyl-4-androstene-3,17-diketone comprises the step oftaking a compound 1 as a starting raw material, carrying out hydrogenation and condensation reaction by using the one-pot method, thus obtaining a 19-desmethyl-4-androstene-3,17-diketone coarse product 3, wherein reaction formulas are as follows: as shown in the specification. According to the method, the high-purity 19-desmethyl-4-androstene-3,17-diketone coarse product can be obtained under a total mole yield of 92 percent or above, so that the method is low in cost, environmentally friendly and suitable for 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-androstene-3,17-dione in one pot. Background technique [0002] Acidic decarboxylation, chemical name: 19-nor-4-androstene-3,17-dione method, can be used to synthesize nomegestrol, norgestrel, norethindrone, is an important steroid body drug intermediates. [0003] 19-nor-4-androstene-3,17-dione: [0004] [0005] Several routes for preparing 19-nor-4-androstene-3,17-dione in the prior art: [0006] 1. US2774777 reported that 19-nor-4-androstene-3,17-dione was obtained through 4 steps of reaction using estrone as the starting material, and the reaction equation is as follows: [0007] [0008] The birch reaction in this route is a low-temperature reaction that requires high equipment, and ammonia gas is used at the same time. Ammonia gas is flammable, toxic, and irritating, and is harmful to operators and the environment. Moreover, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 陈德家林伟戴静邵武
Owner ZHEJIANG XIANJU PHARMA
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