Synthesis method of N-tertiary butyl-3-carbonyl-4-aza-5 alpha-androl-1-end-17 beta-formamide

A technology of tert-butyl and formamide, which is applied in the field of synthesizing the steroid drug finasteride, can solve the problems of lack of novelty, many reaction steps, expensive sulfide, etc., and achieve convenient crystallization and purification, fewer reaction steps, and cheap raw materials Effect

Inactive Publication Date: 2006-01-11
WUHAN UNIV
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Problems solved by technology

The main problems in the above method: counting the preparation of 2, there are too many reaction steps in this method; the preparation of 5 from 4 needs to use expensive toxic sulfide
[0013] In 1996, Zheng Jinhong and others took the lead in publishing the synthesis of finasteride with pregnenolone as a raw material (see the papers published in the "Pharmaceutical Industry" magazine in 1996...

Method used

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  • Synthesis method of N-tertiary butyl-3-carbonyl-4-aza-5 alpha-androl-1-end-17 beta-formamide

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Embodiment 1

[0031] 1. 5,17-dicarbonyl-3,5-cyclo-androst-3-acid (3)

[0032] 4-androstene-3,17-dione (2) 4.0g, tert-butanol 100ml, dropwise add potassium permanganate 0.54g, anhydrous potassium carbonate 4.0g, sodium periodate 16.9g at 50-60°C The aqueous solution was added, and the reaction was maintained at 50-60°C for 3h. Cool to room temperature and filter off the solid. Most of the tert-butanol was evaporated from the filtrate under reduced pressure, and the residual liquid was adjusted to about pH 2 with 6 mol / L hydrochloric acid in an ice bath. Extracted with dichloromethane, dried over anhydrous sodium sulfate, and evaporated to dryness to give white solid 3 (3.8 g, 91.2%), IR (KBr): 3050-3500, 1735, 1702.

[0033] 2. 4-aza-5-androstene-3,17-dione (4)

[0034] 3.8g of the above product (3), 2.9g of ammonium acetate, 40ml of glacial acetic acid, stirred and heated to reflux for 4h, evaporated to remove the acetic acid, poured the residue into water, washed the precipitate with su...

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Abstract

A process for synthesizing N-tert-butyl-3-carbonyl-4-a2Q-5 alpha-androst-1-ene-17 beta-formamide, that is phenandrostamine, includes such steps as providing 4-androstene-3, 17-dione as raw material, oxidizing for opening loop to obtain 5, 17-dicarbonyl-3, 5-openloop-androst-3-acid, reacting on ammonium acetate for closing loop to obtain 4-azasterol compound, cyanoalcoholizing, dewatering, Ritter reaction on tert-butanol, hydrogenating and dehydrogenating.

Description

technical field [0001] The invention relates to a method for synthesizing the steroid drug finasteride (namely, N-tert-butyl-3-carbonyl-4-aza-5α-androst-1-ene-17β-carboxamide). Background technique [0002] Finasteride, a 5α-reductase inhibitor, is a new type of specific drug for the treatment of benign prostatic hyperplasia (BPH). Its chemical name is: N-tert-butyl-3-carbonyl-4-aza-5α-androst-1-ene-17β-carboxamide, its molecular formula is: C22H36N2O2, and its structural formula is: [0003] [0004] Existing synthetic method mainly contains the synthetic method (US Patent: 4760071) of people such as Merck company Rasmusson, and its route is: [0005] [0006] 2 can be synthesized from pregnenolone (see J Med Chem 1984, 27, 1690-1701). The main problems in the above-mentioned method are: including the preparation of 2, the method has too many reaction steps; the preparation of 5 from 4 requires the use of expensive and toxic sulfides. [0007] On the basis of the a...

Claims

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Application Information

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IPC IPC(8): C07J3/00
Inventor 姜中兴叶景泉李乾
Owner WUHAN UNIV
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