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Method for preparing prednisolone

A technology for prednisolone and products, which is applied in the field of chemical preparation, can solve the problems of long process route, unfriendly environment, and many by-products of prednisolone, and achieves low cost, short process route, and improved selectivity. Effect

Inactive Publication Date: 2016-07-27
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the invention is to solve the technical problems that the present preparation of prednisolone has a long process route, low yield, many by-products, high cost and unfriendly environment

Method used

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  • Method for preparing prednisolone
  • Method for preparing prednisolone
  • Method for preparing prednisolone

Examples

Experimental program
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Embodiment 1

[0059] The first step, ethylene glycol protection reaction: add ethylene glycol (150mL, 2.70mol) and triethyl orthoformate (300mL, 1.80mol), cyclohexane 600mL and p-toluenesulfonic acid (1.5g , 9.48mmol), heated to reflux, reacted for 2 hours, distilled ethanol-cyclohexane azeotrope at normal pressure, added 300mL cyclohexane when the solvent was evaporated, refluxed for 1 hour, and distilled ethanol-cyclohexane azeotrope at normal pressure Ethane azeotrope, when no solvent is evaporated, heated to 100°C, distilled under reduced pressure for 2 hours, cooled to room temperature to obtain active ester, protected by nitrogen for use. Under the protection of nitrogen, add dihydroxyprogesterone dehydrogenate 1 (10 g, 29.1 mmol) into a 500 mL reaction flask, add 100 mL of tetrahydrofuran and 10 mL of concentrated hydrochloric acid, add 10 mL of active ester at room temperature, and react at 25 °C for 3 hours. Stop the reaction when there is no raw material point detected by TLC (thi...

Embodiment 2

[0067] The first step, propylene glycol protection reaction: (1) Add 1,3-propanediol (150mL, 2.08mol), triethyl orthoformate (150mL, 0.90mol), 400mL cyclohexane and p-toluenesulfonic acid in a 2000mL reaction flask (1.5g, 8.71mmol), heated to reflux, reacted for 2 hours, fractionated ethanol-cyclohexane azeotrope at normal pressure, added 200mL of cyclohexane when no solvent was evaporated, refluxed for 1 hour, fractionated at normal pressure Ethanol-cyclohexane azeotrope, when no solvent is evaporated, heated to 100°C, distilled under reduced pressure for 2 hours, cooled to room temperature to obtain active ester, protected by nitrogen for use. (2) Under nitrogen protection, add dihydroxyprogesterone dehydrogenate 1 (10g, 29.1mmol), 291mL tetrahydrofuran and 10mL phosphoric acid in a 500mL reaction flask, add 12mL active ester at room temperature, and react at 30°C for 6 hours. Stop the reaction when there is no raw material point detected by TLC, add saturated aqueous sodium...

Embodiment 3

[0070] The first step, neopentyl glycol protection reaction: (1) Add neopentyl glycol (150mL, 1.53mol), triethyl orthoformate (450mL, 2.70mol), cyclohexane 800mL and p-toluene into a 2000mL reaction flask Sulfonic acid (4.5g, 26.13mmol), heated to reflux, reacted for 2 hours, distilled ethanol-cyclohexane azeotrope at normal pressure, added 400mL cyclohexane when no solvent was evaporated, refluxed for 1 hour, normal pressure Fractionally distill the ethanol-cyclohexane azeotrope, and when no solvent is evaporated, heat to 100°C, distill under reduced pressure for 2 hours, and cool to room temperature to obtain the active ester, which is protected under nitrogen for use. (2) Under nitrogen protection, add dihydroxyprogesterone dehydrogenate 1 (10g, 29.1mmol), 60mL tetrahydropyran and 10mL perchloric acid in a 250mL reaction bottle, add 8mL active ester at room temperature, and react at 20°C for 4 Hour. Stop the reaction when there is no raw material point detected by TLC, add...

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Abstract

The invention discloses a method for preparing prednisolone. The method comprises the steps as follows: a dihydroxyprogesterone dehydrogenated substance is adopted as a raw material, an alpha hydroxyl in the 11th position is firstly transformed into beta hydroxyl, then reactions including iodination, replacement and the like are performed, and prednisolone and a derivative of prednisolone are obtained; the equation is shown in the specification. According to the method, the dihydroxyprogesterone dehydrogenated substance is adopted as the raw material for the first time for preparing prednisolone and the derivative of prednisolone, the total yield is 80% or higher, the production cost is reduced, and the method is applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing prednisolone. Background technique [0002] Prednisolone is a very important class of corticosteroids that act on glucose metabolism and reduce the pathological responses of body tissues to damaging stimuli. It is mainly used for various acute severe bacterial infections, various adrenal insufficiency, etc. The structural formula of prednisolone is: [0003] Several routes about preparing prednisolone and derivatives thereof in the prior art: [0004] 1. Process compilation: Pregnancy dienolone acetate synthesizes hydrocortisone through 7 steps, and hydrocortisone is dehydrogenated by biological fermentation to obtain prednisolone, with a total yield of about 20%. This traditional process has a long route and low yield, and because hydrocortisone biofermentation dehydrogenation is difficult to completely convert, and its properties are close to predn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0053
Inventor 陈德家戴静袁云方伟明
Owner ZHEJIANG XIANJU PHARMA
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