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Method for synthesizing progesterone midbody 3beta-hydroxy-5-pregnene-20-ketone

A synthesis method, the technology of pregnene, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of large amount of catalyst active nickel and difficult control, and achieve the effects of reducing refining processes, improving safety, and easy reaction control

Active Publication Date: 2013-03-13
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In the traditional synthesis process of progesterone intermediate 3β-hydroxy-5-pregnene-20-one, it is difficult to control the production process of the catalytic hydrogenation process, and the amount of catalyst active nickel is too large, and excessive hydrogen absorption will inevitably occur, resulting in 20 The ketone group is converted to the unwanted C 20 (R), C 20 (S)-Hydroxyl mixture

Method used

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  • Method for synthesizing progesterone midbody 3beta-hydroxy-5-pregnene-20-ketone
  • Method for synthesizing progesterone midbody 3beta-hydroxy-5-pregnene-20-ketone
  • Method for synthesizing progesterone midbody 3beta-hydroxy-5-pregnene-20-ketone

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Embodiment 1

[0031] 1. Preparation of compound 3β-hydroxy-5,16-pregnadiene-3-acetate-20,20-ethylenedioxy (Ⅲ)

[0032] First, add 450kg of dichloromethane, 150kg of triethyl orthoformate, 150kg of ethylene glycol, 50kg of dienolone acetate, and 2.5kg of pyridine hydrochloride into the reactor, stir well and keep warm at 20°C React for 5 hours; after the reaction is completed, lower the temperature to below 5°C, start adding triethylamine dropwise, control the temperature at 5°C to 10°C, and stir for 30 minutes after adding; Methanol entrainment, after evaporating methanol to dryness, add 50kg of methanol and reflux for 30 minutes; under reflux, add 150kg of pure water dropwise, and then reflux for 1 hour after adding; cool down to below 5°C, continue to stir for 30 minutes, and let it stand for more than 2 hours , centrifuged to dry, washed with water and dried to obtain 55.7kg of compound (Ⅲ).

[0033] 2. Preparation of compound 3β-hydroxy-5-pregnene-3-acetate-20,20-ethylenedioxy (IV)

...

Embodiment 2

[0038]1. Preparation of compound 3β-hydroxy-5,16-pregnadiene-3-acetate-20,20-ethylenedioxy (Ⅲ)

[0039] First, 550kg of chloroform, 150kg of triethyl orthoformate, 180kg of ethylene glycol, 50kg of dienolone acetate, and 1.8kg of p-toluenesulfonic acid were added to the reactor, stirred evenly and placed in the reactor at 25 ℃ for 4 hours to react; after the reaction is completed, lower the temperature to below 5 ℃, start adding triethylamine dropwise, control the temperature at 5 ℃ ~ 10 ℃, and stir for 30 minutes after the addition; evaporate all solvents under reduced pressure, and then use Entrained with 20kg of methanol, evaporated to dryness, added 50kg of methanol and refluxed for 30 minutes; under reflux, added dropwise 150kg of pure water, and refluxed for 1 hour after addition; cooled to below 5°C, continued to stir for 30 minutes, and stood for 2 After more than 1 hour, it was centrifuged to dry, washed with water and dried to obtain 55.5kg of compound (Ⅲ).

[0040]...

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Abstract

The invention relates to a method for synthesizing progesterone midbody 3beta-hydroxy-5-pregnene-20-ketone. By the method, a refining procedure and a by-product oxidation recovery processing procedure of a traditional synthesizing process are saved. The obtained midbody does not need to be refined, the once quality yield is more than 86%, and the product purity is more than 99.0%.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing a progesterone intermediate 3β-hydroxyl-5-pregnene-20-one. Background technique [0002] Progesterone (4-pregnene-3,20-dione) has the structural formula: [0003] [0004] Progesterone is a progestin drug and an important intermediate. The traditional synthesis process of progesterone intermediate 3β-hydroxy-5-pregnene-20-one is based on dienolone acetate as raw material, and 3β-hydroxy-5-pregnene is obtained in the presence of hydrogen and active nickel in ethanol. sterene-20-one-3-acetate, and then through alkali hydrolysis to obtain the crude product of the intermediate - 3β-hydroxy-5-pregnene-20-one, which contains about 5% impurities, and needs Refined to a content of 98.5% or more before the next step of the Wöhler oxidation reaction of progesterone. [0005] [0006] About 4% of the impurity in the crude 3β-hydrox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 王勇李新宇付林廖俊徐勇
Owner HUAZHONG PHARMA
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