Synthesis method of main impurities of dehydropregnenolone acetate

A technology of dienolone acetate and diketene acetate is applied in the field of synthesis of main impurities of diketene acetate, can solve the problems of long time consumption, low purity and the like, and achieves a short synthesis time and high product purity. Effect

Inactive Publication Date: 2015-05-13
湖北竹溪人福药业有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Some foreign scholars have obtained compound I by reacting dienolone acetate and potassium dichromate in a solution of glacial acetic acid and acetic anhydride for 48 hours. relatively low

Method used

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  • Synthesis method of main impurities of dehydropregnenolone acetate
  • Synthesis method of main impurities of dehydropregnenolone acetate
  • Synthesis method of main impurities of dehydropregnenolone acetate

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Experimental program
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Effect test

Embodiment 1

[0025] Add 200ml of benzene and 10.0g of dienolone acetate into the three-necked flask, add 50g of pyridinium dichromate, 15ml of tert-butanol peroxide, and 5.0g of diatomaceous earth under stirring, and stir for 2 hours at 20°C. Filter through a diatomaceous earth funnel, collect the filtrate, evaporate the filtrate under reduced pressure to remove the solvent, concentrate and dry the filtrate to obtain the crude product of compound I, add 5ml of dichloromethane to dissolve the crude product, and separate by chromatography column to obtain compound I, chemical name: 3β-acetoxy -pregna-5,16-diene-7,20-dione, the structure of which is shown in Formula I. The chromatographic column material is 200 mesh silica gel, and the eluent is: cyclohexane: ethyl acetate = 2:1 (V:V).

[0026]

[0027] It is a white powder product, 7.5 g, yield: 75%; HPLC: 98.2%.

[0028] MS (mz): 370 (M+).

[0029] 1 HNMR (CDCl 3 ): δ: 0.90 (3H, s, 18-CH 3 ), 1.20 (3H, s, 19-CH 3 ), 1.25, 1.9, 0 (e...

Embodiment 2

[0032] Add 500ml of benzene and 20.0g of dienolone acetate into the three-necked flask, add 140g of pyridinium dichromate, 34ml of tert-butanol peroxide, and 16.0g of diatomaceous earth under stirring, stir at 25°C for 3h, and use a Filter through a diatomaceous earth funnel, collect the filtrate, evaporate the filtrate under reduced pressure to remove the solvent, and dry the filtrate to obtain the crude product of compound I. Add 16ml of dichloromethane to dissolve the crude product, and separate by column chromatography to obtain compound I. The white powder product is 15.2g, and the yield is : 76%; HPLC: 98.5%. The chromatographic column material is silica gel, and the eluent is: cyclohexane:ethyl acetate=3:1 (V:V).

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Abstract

The invention relates to a synthesis method of main impurities of dehydropregnenolone acetate. The synthesis method comprises the following steps: dissolving dehydropregnenolone acetate in benzene, stirring and adding tert-butyl hydroperoxide, pyridinium dichromate and kieselguhr, reacting for 2-3h at a room temperature, filtering materials, concentrating a filtrate to obtain a compound I crude product; adding dichloromethane to dissolve the crude product; and carrying out chromatographic column separation to obtain a compound I. The method is simple and rapid in process and high in product purity, and the product can be used as a standard substance and used for optimizing a production process for dehydropregnenolone acetate and improving the qualities of diene products.

Description

technical field [0001] The invention relates to a method for synthesizing main impurities of dienolone acetate. Background technique [0002] Diene, English name: 16-pregnadien-20-one acetate, chemical name: 3β-hydroxy-pregnadien-5,16-diene-20-one-3-acetate, molecular formula C23H32O3. Diene is a structural intermediate of steroid hormones, which can be used to synthesize adrenal hormones, steroidal anti-inflammatory drugs, glucocorticoids, sex hormones and other drugs. Domestic manufacturers generally use diosgenin as raw material to synthesize dienes through ring-opening acylation and oxidative hydrolysis. The reaction equation is as follows: [0003] [0004] In the production of dienolone acetate, the content of dienolone acetate has been around 98% due to repeated application of the mother liquor and excessive oxidation. Some foreign scholars have obtained compound I by reacting dienolone acetate and potassium dichromate in a solution of glacial acetic acid and ace...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J13/00
CPCC07J13/005
Inventor 周建生杨艳青郑建雄常文胜侯海波
Owner 湖北竹溪人福药业有限责任公司
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