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Synthetic method of 16alpha-hydroxy prednisonlone

A technique for the synthesis of hydroxyprednisolone, which is applied in the fields of steroids and organic chemistry, and can solve the problems of long synthesis steps and complex post-processing of products, and achieve the effects of high efficiency, convenient post-processing, and high production capacity

Inactive Publication Date: 2010-11-03
无棣鑫岳化工集团有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the existing synthetic route, the synthetic steps are long and the post-processing of the product is complicated

Method used

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Abstract

The invention discloses a synthetic method of 16alpha-hydroxy prednisonlone as shown in formula (III), comprising the following steps: taking the prednisonlone as shown in formula (I) as a raw material; carrying out dehydration reaction to generate a double bond in acidic ionic liquid as shown in formula (II); adding hydrogen peroxide aqueous solution to react; and adding water for further hydrolyzation after full reaction to finally obtain the 16alpha-hydroxy prednisonlone. The synthetic method of the invention adopts the property of the acidic ionic liquid as a reaction medium as well as a catalyst and changes technological conditions such as reaction time, reaction temperature and the like, thus achieving the purpose of reduced cost, energy conservation and emission reduction, and being applicable to industrial production.

Description

(1) Technical field The invention relates to a method for synthesizing 16α-hydroxyprednisolone. (2) Background technology 16α-Hydroxyprednisolone, chemical formula: C 21 h 28 o 6 , molecular weight: 376.44. It is an important intermediate of ciclesonide, a drug for treating asthma. Regarding the synthesis of 16α-hydroxyprednisolone, the methods reported at present all use prednisolone as a raw material, and form a ring with triethyl orthoacetate under the catalysis of pyridinium p-toluenesulfonate, and selectivity under weakly acidic conditions Ring-opening to obtain acetylated products, and then reacting with acetic anhydride under alkaline conditions to form diacetylated products, heating in the presence of potassium acetate to remove a molecule of acetic acid to obtain (11β)-hydroxy-21-acetoxy-1,4, 16-Pregnatriene-3,20-dione compound. The compound is selectively dihydroxylated under the action of potassium permanganate, and deacetylated in the presence of sodium hyd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
Inventor 裴文孙莉王海滨郑洁潘海燕胡香凝
Owner 无棣鑫岳化工集团有限公司
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