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Preparation method of 19-demethylation-4-androstenedione

A technology for androstenedione and demethylation is applied in the field of preparation of 19-desmethyl-4-androstenedione, which can solve the problems of large amount of solvent and water, large environmental pollution, temperature sensitivity, etc. The effect of product external standard and appearance, less environmental pollution, and easy control

Inactive Publication Date: 2017-07-07
上海津力药业股份有限公司
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Problems solved by technology

[0003] The technical problem to be solved by the present invention is: provide a kind of preparation method of 19-desmethyl-4-androstenedione, it solves the process of preparing 19-desmethyl-4-androstenedione at present, to The environmental pollution is relatively large, the amount of solvent and water is relatively large, it is sensitive to temperature, difficult to control, and the yield is not high

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  • Preparation method of 19-demethylation-4-androstenedione

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[0020] In order to understand the technical means, creative features, goals and effects of the present invention easily, the present invention will be further described below in conjunction with the accompanying drawings.

[0021] Such as figure 1 Shown, the step flow chart of this preparation method.

[0022] A preparation method of 19-desmethyl-4-androstenedione, comprising the following steps:

[0023] (1) Esterification: At room temperature, add 200ml of acetic anhydride, 6g of p-toluenesulfonic acid, and 10g of 4AD (4-androstenedione) into a clean three-neck flask, stir and clarify, and control the system at 20-25°C React for 5 hours. After the reaction is detected by TCL, cool down the system to 0-5°C, slowly pour 200ml of ice water into the system, keep stirring at 0-5°C for 2 hours, filter with suction, wash with a large amount of water until neutral, vacuum 40 After drying at ℃, 10.74 g of off-white solid esterified product was obtained, with a purity of 98.0% (area...

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Abstract

The invention discloses a preparation method of 19-demethylation-4-androstenedione and belongs to the technical field of medical intermediate processing. The preparation method comprises the following steps: (1) carrying out esterification reaction; (2) carrying out ketalation; (3) carrying out reduction reaction; (4) carrying out hydrolysis reaction; (5) carrying out esterification reaction; (6) carrying out addition reaction; (7) carrying out cyclization and hydrolysis reaction; (8) carrying out oxidation, dechloridation and ring-opening reaction; and (9) carrying out oxidation and decarboxylation reaction. The preparation method disclosed by the invention has the advantages that environmental pollution is small, usage amounts of a solvent and water are smaller, temperature sensitivity is low, control is easy, and yield is high; a chlorinating agent is adopted, so that reaction yield is increased; 1,3-dichloro-5,5-dimethylhydantoin is adopted, so that the reaction yield is further increased; and sodium hydrogen carbonate is adopted, so that final decarboxylic reaction yield is increased, and external standards and appearance of a product can be improved.

Description

technical field [0001] The invention relates to a preparation method of 19-desmethyl-4-androstenedione, belonging to the technical field of pharmaceutical intermediate processing. Background technique [0002] At present, the preparation method of 19-desmethyl-4-androstenedione is that acetic acid pregnant dienolone needs to undergo oximation and Bergmann rearrangement to obtain a rearrangement, and the rearrangement is through an addition reaction, Cyclization, hydrolysis, oxidation, dechlorination, ring opening, oxidation, decarboxylation, and finally 19-desmethyl-4-androstenedione can be obtained. But acetic acid pregnant dienolone raw material is bigger to environmental pollution, and in carrying out oximation, the consumption of solvent and water in the reaction of Beckmann rearrangement is bigger, is more sensitive to temperature, is difficult to control, and yield is not high, in addition The phosphorus oxychloride required for the reaction is a regulated highly toxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 黄金龙王海峰
Owner 上海津力药业股份有限公司
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