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Production method for synthetizing epiandrosterone from single enol ketone acetate

A monoenolone acetate and a production method technology, applied in the chemical industry, can solve the problems of incomplete reaction of intermediate products, harsh hydrogenation reaction conditions, and many by-products, and achieve simple reaction process, simple preparation method, and low by-products little effect

Active Publication Date: 2013-05-15
湖北民生生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the hydrogenation process, palladium chloride-calcium carbonate is used as a catalyst to carry out the hydrogenation reaction. The hydrogenation reaction conditions of this production method are harsh and difficult to control. It is easy to cause incomplete reaction of intermediate products and many by-products, which will bring great harm to the next step of hydrolysis reaction. impact, the purity of the crude product after hydrolysis is only about 80%, and to obtain a high-purity product, multiple recrystallization methods must be used, resulting in a low yield
The overall yield of this production method is reported to be only 54%

Method used

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  • Production method for synthetizing epiandrosterone from single enol ketone acetate
  • Production method for synthetizing epiandrosterone from single enol ketone acetate
  • Production method for synthetizing epiandrosterone from single enol ketone acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 1) Preparation of Ketoxime III

[0030] Add 300ml of ethanol, 48ml of pyridine, 24g of hydroxylamine hydrochloride, and 80g of monoenolone acetate II to the reaction flask in sequence, heat up, and time the reflux reaction for 4 hours. After the reflux is completed, cool down to 0°C and separate by suction filtration until no liquid flows out. Rinse with ethanol, then wash with water until neutral, filter and dry with suction to obtain ketoxime III 78.4g.

[0031] 2) Preparation of rearrangement IV

[0032] Add 600ml of dehydrated pure benzene and 75g of ketoxime III to the reaction bottle in turn, stir at room temperature to dissolve, then cool down to 5°C, slowly add phosphorus oxychloride-pure benzene mixture dropwise (37.5ml phosphorus oxychloride-75ml) , The temperature of the dropping process is controlled at 5-10°C, and the dropping is completed in 2 hours. Control the temperature at 10-15°C and keep it warm for 2 hours, lower the temperature to 5°C, slowly add...

Embodiment 2

[0036] 1) Preparation of Ketoxime III

[0037] Add 600ml of ethanol, 96ml of pyridine, 48g of hydroxylamine hydrochloride, and 160g of monoenolone acetate II to the reaction flask in sequence, heat slowly, and time reflux for 4 hours. After the reflux, the temperature was lowered to 0°C, and the material was separated by suction filtration. The material was washed with ethanol until no liquid flowed out, and then washed with water until neutral, drained and dried to obtain 158.2 g of ketoxime III.

[0038] 2) Preparation of rearrangement IV

[0039] Add 1200ml of dehydrated pure benzene and 150g of ketoxime III to the reaction bottle in turn, stir at room temperature to dissolve, then cool down to 5°C, slowly add phosphorus oxychloride-pure benzene mixture (75ml phosphorus oxychloride-150ml pure benzene ), the temperature of the dropping process should be controlled at 5-10°C, and the dropping should be completed in 2 hours. Control the temperature at 10-15°C, hold the react...

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Abstract

The invention provides a production method for synthetizing epiandrosterone from single enol ketone acetate. The production method comprises the steps of: taking single enol ketone acetate as a material, and obtaining epiandrosterone by oximating, rearrangement and hydrolysis reaction, wherein the purity can be up to over 98.5%; and the yield achieves over 68%. Hydrogenation is saved; the problem of high industrial cost due to the fact that palladium chloride-calcium carbonate is taken as a catalyst in the traditional method is solved; the product yield is improved; and the process has the characteristics of being simple to operate, small in pollution, high in yield and the like, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and relates to a preparation method of a steroid hormone pharmaceutical compound, in particular to preparing epiandrosterone from monoenolone acetate. Background technique [0002] Epiandrosterone, chemical name 5α-androst-3β-ol-17-one, CAS number 481-29-8, molecular formula C 19 h 30 o 2 . The structural formula is: [0003] [0004] Epiandrosterone is an important intermediate in the synthesis of androgenic anabolic hormones, corticosteroids and other steroid drugs. [0005] The existing production process of epiandrosterone is to use dienolone acetate, that is, 5,16-pregnadiene-3-acetate-20-one as the starting material, through oximation, rearrangement, hydrolysis, hydrogenation , five-step hydrolysis synthesis. Due to the presence of a △5⑹-position double bond in the diene structure, epiandrosterone needs to be hydrogenated to obtain epiandrosterone. In the hydrogenation process, pa...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 陈少华裴胜汛
Owner 湖北民生生物医药有限公司
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