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Method for preparing canrenone as spironolactone intermediate

A canrenone and intermediate technology, applied in the field of canrenone preparation, can solve the problems of high corrosiveness, harsh reaction conditions, and high equipment requirements, and achieve the effects of low equipment requirements, simple reaction conditions, and low waste.

Inactive Publication Date: 2019-12-20
ZHEJIANG SHENZHOU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the deficiencies of the prior art, the present invention provides a method for preparing spironolactone intermediate canrenone. The method has the advantages of simplicity, high efficiency, low production cost, and is suitable for large-scale industrial production, and solves the problem of the preparation of canrenone on the market. Harsh reaction conditions, high corrosiveness, high requirements for equipment, difficult operation, low yield and high cost

Method used

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  • Method for preparing canrenone as spironolactone intermediate
  • Method for preparing canrenone as spironolactone intermediate

Examples

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Effect test

Embodiment 1

[0018] A method for preparing spironolactone intermediate canrenone, the process of the preparation method is:

[0019] Add 5 grams of potassium hydroxide to 70 milliliters of methanol, stir and dissolve under nitrogen protection, then add 10 grams of 7α-hydroxylactone, control the temperature at 5°C for 7 hours, adjust the pH to neutral with acetic acid, concentrate, and add 100 milliliters water, filtered, and refined with methanol to obtain 8.5 g of canrenone.

Embodiment 2

[0021] A method for preparing spironolactone intermediate canrenone, the process of the preparation method is:

[0022] Add 10 grams of 7α-hydroxylactone to 60 ml of dichloromethane, stir and dissolve under nitrogen protection, add 15 ml of triethylamine, control the temperature at about 0°C, add 12 ml of methanesulfonyl chloride dropwise to react for 4 hours, add 50 ml of water The organic layer was washed, dichloromethane was concentrated, and methanol was crystallized to obtain 8.6 g of canrenone.

Embodiment 3

[0024] A method for preparing spironolactone intermediate canrenone, the process of the preparation method is:

[0025] Add 10 g of 7α-hydroxylactone to 50 ml of dichloromethane, stir and dissolve under nitrogen protection, add 18 ml of pyridine, control the temperature at about 5°C, add dropwise 13 ml of trifluoroacetic anhydride to react for 5 hours, add 50 ml of water to wash The dichloromethane layer was concentrated, and crystallized from methanol to obtain 8.4 g of canrenone.

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Abstract

The invention relates to the technical field of canrenone preparation, and particularly discloses a method for preparing canrenone as a spironolactone intermediate. The method for preparing the canrenone as the spironolactone intermediate specifically comprises the steps that a biological fermentation product 7alpha-hydroxylactone is used as a raw material, a 6,7-site double-bond is formed, and the canrenone as the spironolactone intermediate is obtained. The method for preparing the canrenone as the spironolactone intermediate is simple and efficient and low in the production cost, suitable for large-scale industrial production and convenient for people to use.

Description

technical field [0001] The invention belongs to the technical field of canrenone preparation, in particular to a method for preparing spironolactone intermediate canrenone. Background technique [0002] Canrenone, whose chemical name is 17β-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylate-γ-lactone, is both a commonly used diuretic and a synthetic spironolactone , drospirenone, eplerenone and other key intermediates, its efficient and simple preparation process is of great significance for the synthesis of downstream products. [0003] At present, there are mainly two methods for the synthesis of 6,7-double bonds. One is to use lactones as raw materials to form 6,7-double bonds through bromination and dehydrobromination to obtain canrenone. The reaction conditions are harsh, corrosive, high requirements on equipment, difficult to operate, large amount of three wastes, low yield and high cost. The second method is to use lactone as raw material, through etherification and d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J21/00
CPCC07B2200/07C07J21/003
Inventor 王友富王荣王炳乾王洪福邵振平雷灵芝黄橙橙王瑞陈克纲应杨波
Owner ZHEJIANG SHENZHOU PHARMA
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