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Method for preparing 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative from mother solution reclaimed materials of hydrogenation reaction

A technology for recovering carboxylic acid derivatives and mother liquor, applied in steroids, organic chemistry, etc., can solve problems such as waste of the environment, pollution, etc., and achieve the effect of reducing pollution and reducing costs

Active Publication Date: 2015-02-25
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems of waste and environmental pollution caused by the incineration of the mother liquor reclaimed material in the hydrogenation reaction of 3-carbonyl-4-aza-5-androstene-17β carboxylic acid derivatives in the prior art, the purpose of the present invention is to provide a method that is simple and low cost. Inexpensive, suitable for industrial production, the method for preparing 3-carbonyl-4-aza-5-androstene-17β carboxylic acid derivative 01 using the recovered material of the mother liquor of the hydrogenation reaction, this process has not been reported in the literature

Method used

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  • Method for preparing 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative from mother solution reclaimed materials of hydrogenation reaction
  • Method for preparing 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative from mother solution reclaimed materials of hydrogenation reaction
  • Method for preparing 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative from mother solution reclaimed materials of hydrogenation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Dehydrogenation reaction to prepare methyl 3-carbonyl-4-aza-5-androstene-17βcarboxylate 01

[0057] The preparation method comprises the following steps:

[0058] (1) Hydrogenation of 3-carbonyl-4-aza-5-androstene-17β carboxylic acid derivative 01 to prepare the mother liquor of 3-carbonyl-4-aza-5α-androstene-17β carboxylic acid derivative 03 The reclaimed material is used as a raw material, and the raw material is dissolved in glacial acetic acid, a palladium carbon catalyst is added, oxygen is passed through, pressurized, and the temperature is raised to carry out a dehydrogenation reaction;

[0059] The specific operation method is: at room temperature, in a 2000ml stainless steel hydrogenation reactor equipped with a thermometer and a stirrer, add glacial acetic acid 1200ml, stir, add the hydrogenation mother liquor reclaimed material (3-carbonyl- 4-aza-5α-androsta-17β-carboxylate methyl ester (03) and 3-carbonyl-4-aza-5β-androsta-17β-carboxylate methyl e...

Embodiment 2

[0068] Identical with embodiment 1, difference only is: in step (1), described palladium carbon catalyst is the palladium carbon that mass content is 1%; Described hydrogenation mother liquor reclaimed material, glacial acetic acid and palladium carbon catalyst are 1 by mass ratio: 8:0.1; the oxygen pressure is 0.2MPa; the reaction temperature is 120°C; the reaction time of the dehydrogenation reaction is 18 hours. In step (3), methanol is added to the system, and the mass ratio of the hydrogenation mother liquor reclaimed material to methanol is 1:1.

[0069] HPLC detection: the purity of 01 is 95.2623%; the content of 03 is 0.2457%.

Embodiment 3

[0071] Identical with embodiment 1, difference only is: in step (1), described palladium carbon catalyst is the palladium carbon that mass content is 25%; Described hydrogenation mother liquor reclaimed material, glacial acetic acid and palladium carbon catalyst are 1 by mass ratio: 20:0.3; the oxygen pressure is 0.8 MPa; the reaction temperature is 160° C.; the reaction time of the dehydrogenation reaction is 30 hours. In step (3), methanol is added to the system, and the mass ratio of the hydrogenation mother liquor reclaimed material to methanol is 1:3.

[0072] HPLC detection: the purity of 01 is 96.1524%; the content of 03 is 0.2916%.

[0073] Comparative experiment Preparation of methyl 3-carbonyl-4-aza-5-androstene-17βcarboxylate (01)

[0074] The specific operation method is:

[0075] At room temperature, in a 1000ml glass reaction flask equipped with a thermometer and a stirrer, add 600ml of the obtained filtrate obtained from the filtrate to be concentrated after f...

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Abstract

The invention provides a method for preparing 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative 01 from mother solution reclaimed materials of a hydrogenation reaction. The method comprises the following steps: (1) dissolving the mother solution reclaimed materials, which are obtained by preparing 3-carbonyl-4-aza-5 alpha-androstane-17 beta carboxylic acid derivative 03 by performing hydrogenation reaction on 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative 01, into glacial acetic acid, and adding a palladium-carbon catalyst, introducing oxygen, pressurizing and heating to perform dehydrogenation reaction; (2) cooling the reaction system, filtering to obtain a filter cake, washing the filter cake by using glacial acetic acid, and performing suction filtration until the filter cake is dried, thereby obtaining a waste palladium-carbon filter cake; and (3) performing vacuum concentration on a filtrate until the filtrate is almost dried, adding methanol into the system, performing freezing crystallization, performing swinging filtration to obtain a filter cake, washing the filter cake by using methanol, performing swinging filtration until the filter cake is dried, and drying to obtain the 3-carbonyl-4-aza-5-androstene-17 beta carboxylic acid derivative 01. By adopting the method provided by the invention, wastes are recycled to synthesize an important medical intermediate, the cost is reduced, and pollution is reduced. Original auxiliary materials are simple, easily available and recyclable, and the process is simple and is suitable for industrial implementation.

Description

technical field [0001] The invention relates to a method for preparing a pharmaceutical intermediate 3-carbonyl-4-aza-5-androstene-17β carboxylic acid derivative 01 by using the recycled mother liquor of hydrogenation reaction. Background technique [0002] Finasteride and Dutasteride are drugs for the treatment of benign prostatic hyperplasia and alopecia developed by Merck and Glaxo, respectively, with definite curative effects and few side effects. 3-Carbonyl-4-aza-5α-androst-17βcarboxylic acid derivative 03 is an important intermediate. The 3-carbonyl-4-aza-5-androstene-17β carboxylic acid derivative 01 is hydrogenated to prepare the 3-carbonyl-4-aza-5α-androstene-17β carboxylic acid derivative 03. However, this hydrogenation reaction will inevitably produce 3-carbonyl-4-aza-5β-androst-17βcarboxylic acid derivative 02, that is, the 5β isomer, which will affect the product yield and production cost in the end. . Since 3-carbonyl-4-aza-5-androstene-17β carboxylic acid d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00
CPCC07J73/005
Inventor 左前进甘红星谢来宾
Owner HUNAN KEREY BIOTECH
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