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Method for synthesizing 16 alpha-hydroxy prednisolone

A technology of hydroxyprednisolone and synthetic methods, applied in the direction of steroids, organic chemistry, etc., can solve the problems of key technologies that need to be broken through and the inability to form industrial production, and achieve the effects of low difficulty, easy control, and low pollution

Active Publication Date: 2011-08-10
浙江东晖药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Method 2: Using prednisolone as the starting material, 16α-hydroxyprednisolone is directly produced through microbial fermentation technology, but this method is currently only in the experimental stage, and the key technology needs to be broken through, and industrial production cannot be formed at present

Method used

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  • Method for synthesizing 16 alpha-hydroxy prednisolone
  • Method for synthesizing 16 alpha-hydroxy prednisolone
  • Method for synthesizing 16 alpha-hydroxy prednisolone

Examples

Experimental program
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Effect test

Embodiment 1

[0030] This example introduces a synthetic method for 16α-hydroxyprednisolone. The synthetic steps are as follows: firstly add 40g of prednisone, 240ml of pyridine, and 100ml of acetone into the reaction bottle in turn, and keep the reaction below 0°C to achieve Detected under 254nm ultraviolet light, after the raw material point is less than 1%, water analysis in ice water, standing overnight, suction filtration, washing with water, drying, recrystallization to obtain 31.2g of intermediate I, the chemical formula of intermediate I is:

[0031]

[0032] Take 20g of intermediate I, 11g of potassium permanganate, 2ml of triethylamine, and 1000ml of acetone, and put them into the reaction bottle in turn, react at low temperature, and achieve detection under a 254nm ultraviolet lamp. After the raw material point is less than 1%, add sulfite 5g, terminate the reaction, filter, concentrate under reduced pressure, cool, suction filter, and dry to obtain 20g of intermediate II, the ...

Embodiment 2

[0041] This example introduces a synthesis method of 16α-hydroxyprednisolone. The synthesis steps are as follows: first, add 40 g of prednisone, 240 ml of collidine, and 100 ml of acetone into the reaction bottle in sequence, and keep the temperature below 0°C for reaction , to achieve detection under 254nm ultraviolet light, after the raw material point is less than 1%, water analysis in ice water, standing overnight, suction filtration, washing with water, drying, recrystallization to obtain 31.2g of intermediate I, the chemical formula of intermediate I is:

[0042]

[0043] Take 20g of intermediate I, 11g of osmium tetroxide, 2ml of pyridine, and 1000ml of acetone and put them into the reaction bottle in turn, and react at low temperature until it is detected under a 254nm ultraviolet lamp. After the raw material point is less than 1%, add 5g of sulfite to stop Reaction, filtration, concentration under reduced pressure, cooling, suction filtration, drying to obtain 20g o...

Embodiment 3

[0052] This example introduces a synthetic method for 16α-hydroxyprednisolone. The synthetic steps are as follows: first, add 40 g of prednisone, 120 ml of pyridine, 120 ml of collidine, and 100 ml of acetone into the reaction flask in sequence, The following heat preservation reaction can be detected under a 254nm ultraviolet lamp. After the raw material point is less than 1%, the ice water water analysis, standing overnight, suction filtration, washing with water, drying, recrystallization to obtain 31.2g of intermediate I, the chemical formula of intermediate I for:

[0053]

[0054] Take 20g of intermediate I, 5g of potassium permanganate, 5g of osmium tetroxide, 2ml of collidine, and 1000ml of acetone and put them into the reaction bottle in turn, and react at low temperature to achieve detection under 254nm ultraviolet lamp, and the raw material point is less than 1%. Finally, add sulfite 5g, stop reaction, filter, concentrate under reduced pressure, cool, suction fil...

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Abstract

The invention relates to a method for synthesizing 16 alpha-hydroxy prednisolone, and belongs to the field of chemical technologies. In the method, prednisone is taken as an initiative raw material, and subjected to five-step reaction of elimination, oxidation, condensation, reduction and hydrolysis to form the 16 alpha-hydroxy prednisolone; the prednisone is taken as the raw material, organic weak base is taken as a retarder to inhibit the oxidation rate of potassium permanganate to reactants, a three-phase acid solvent is taken as a solvent, ketoxime is hydrolyzed by adding aqueous solution of nitrite, and refining is carried out by a multiphase separation crystallization technology. The method has the advantages of simple operation, mild reaction conditions, readily available raw material, low cost and light environmental pollution.

Description

technical field [0001] The invention relates to a method for synthesizing 16α-hydroxyprednisolone, which belongs to the field of chemical technology. Background technique [0002] 16α-Hydroxyprednisolone is an important pharmaceutical intermediate of halogen-free adrenal cortex hormone drugs, and is used in the manufacture of desonide, budesonide and ciclesonide for the treatment of bronchial inflammation and asthma drugs The basic raw material, the market prospect is very broad. [0003] At present, there are two kinds of synthetic reports about 16α-hydroxyprednisolone in the literature. Method one: using prednisolone as a starting material, it is prepared through reactions such as cyclic ester, hydrolysis, acylation, elimination and oxidation, but The method starting material prednisone price is higher, the reaction steps are longer and the reaction is repeated, and the cost is higher. Method 2: Using prednisolone as the starting material, 16α-hydroxyprednisolone is dire...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 王勇
Owner 浙江东晖药业有限公司
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