Whorl[(5 beta, 6 beta, 15 beta, 16 beta-dimethylene-androstane-14 beta-hydrogen-5, 7-diene-3-ketone)-17 alpha-2'-(1'-oxygen-cyclopentane-5'-ketone)] and synthesis process

A dimethylene and methylene technology, used in steroids, drug combinations, sexual diseases, etc., can solve problems such as inability to produce, and achieve the effects of easy yield and high development value

Inactive Publication Date: 2008-12-10
SHANGHAI UNIV
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Problems solved by technology

[0005] The disadvantage is that domestic raw materials cannot be used for synthesis. The key intermediate 3β-hydroxy-androst-5,16-d

Method used

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  • Whorl[(5 beta, 6 beta, 15 beta, 16 beta-dimethylene-androstane-14 beta-hydrogen-5, 7-diene-3-ketone)-17 alpha-2'-(1'-oxygen-cyclopentane-5'-ketone)] and synthesis process
  • Whorl[(5 beta, 6 beta, 15 beta, 16 beta-dimethylene-androstane-14 beta-hydrogen-5, 7-diene-3-ketone)-17 alpha-2'-(1'-oxygen-cyclopentane-5'-ketone)] and synthesis process
  • Whorl[(5 beta, 6 beta, 15 beta, 16 beta-dimethylene-androstane-14 beta-hydrogen-5, 7-diene-3-ketone)-17 alpha-2'-(1'-oxygen-cyclopentane-5'-ketone)] and synthesis process

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Embodiment 1

[0024] Embodiment one: concrete steps are as follows:

[0025] 1. Add 15.98 grams of dehydroepiandrosterone, 37.32 grams of ketone bromide and 600 milliliters of methanol into a 1-liter three-neck flask, and heat to reflux for 6-24 hours. Stop the reaction and filter while hot. Methanol was recovered from the filtrate under reduced pressure, water was added, and dichloromethane was extracted with 3×300 ml. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure with a rotary evaporator to obtain a yellow viscous substance, which was recrystallized twice with ethyl acetate to obtain 12.218 g of white needle-like solid 16α- Bromo-3β-hydroxy-androst-5-en-17-one (2), yield: 60%. The structural formula of 16α-bromo-3β-hydroxy-androst-5-en-17-one is:

[0026]

[0027] Molecular formula: C 19 h 21 BrO 2

[0028] Molecular weight: 366.11

[0029] Appearance: white solid

[0030] Infrared spect...

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Abstract

The invention relates to a spiro [(5beta, 6beta, 15beta, 16beta-dimethylene-androstane-14beta-hydrogen-5, 7-diene-3-keton)- 17alpha-2'-(1'-oxygen-cyclopentane-5'-ketone) and a synthetic method thereof. A structural formula of the compound is the right formula; the method begins from cheap and available dehydroepiandrosterone 1 and can fully obtain a product overturned by 14 H of a target product of drospirenone through an eight-step reaction, namely a C14beta-H isomer of the drospirenone; and the unique difference between the isomer and the drospirenone in the structure lies in that 14-H of the isomer is a beta configuration, while 14-H of the drospirenone is an alpha configuration. As the C14beta-H isomer of the drospirenone and the synthetic method are not reported in literature, the C14beta-H isomer of the drospirenone can be a new drug which has the same medicative effect as the drospirenone, has high development value and provides a new strategy for the synthesis of the drospirenone.

Description

technical field [0001] The present invention relates to a kind of steroidal compound and its synthetic method, especially spiro[(5β, 6β, 15β, 16β-dimethylene-androst-14β-hydrogen-5,7-dien-3-one)- 17α-2'-(1'-oxo-cyclopentane-5'-one)] and its synthetic method. Background technique [0002] Steroids are an important class of natural organic compounds that widely exist in biological tissues, sterols, vitamin D, bile acids, many sex hormones, adrenal cortex hormones, some carcinogenic hydrocarbons, steroidal saponins and steroidal alkaloids, etc. fall into this category. Many steroids have been found to have very important physiological roles, so steroid chemistry is naturally one of the most interesting fields in the medical and pharmaceutical industry. Many steroids have special physiological effects. For example, hormones, vitamins, toxins and drugs are important biological regulators. [0003] Drospirenone (DRSP) is derived from 17α spironolactone. Its biochemical and pha...

Claims

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Application Information

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IPC IPC(8): C07J53/00C07J21/00A61P15/16A61P15/18
Inventor 郝健姚尚清万文蒋海珍
Owner SHANGHAI UNIV
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