Methylprednisolone intermediate debrominated product and preparation method thereof

A technology for methylprednisolone and intermediates, applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve the problems of low product purity, long synthetic route, cumbersome operation, etc., and achieve high yield, The effect of short synthetic route and easy access to raw materials

Active Publication Date: 2020-01-17
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] For this reason, what the present invention is to solve is that the synthetic technique of methylprednisolone intermediate debrominated substance has long synthetic route, low yield, high cost, low product purity, and the defects of loaded down with trivial details, and then provides a kind of Debrominated product of methylprednisolone intermediate and preparation method thereof

Method used

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  • Methylprednisolone intermediate debrominated product and preparation method thereof
  • Methylprednisolone intermediate debrominated product and preparation method thereof
  • Methylprednisolone intermediate debrominated product and preparation method thereof

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Embodiment 1

[0035] This embodiment provides a methylprednisolone intermediate and a preparation method thereof. The preparation method comprises the steps of:

[0036] (1) Dechlorination reaction: add 350ml of acetone, 50g of the compound shown in formula I, 15g of zinc powder, and 75ml (78.7g) of glacial acetic acid into the three-necked flask, and heat up to 50-55°C for reflux reaction for 6-7h; TLC Track the reaction. After the reaction is finished, cool the system down to below 35°C, add 350ml of dichloromethane, filter, and wash the filter cake with a small amount of dichloromethane; steam the filtrate to a paste, add 250ml of water, stir at room temperature for 1h, pump Filter, wash with water until neutral, and dry to obtain 42g of the compound shown in formula II. The yield of the compound shown in formula II is 92.8%, and the purity is 95.7% (HPLC). HR-ESI-Ms(M+H): 329.2;

[0037] (2) Bromine reaction: Add 400ml of acetone and 20ml of water into a 1L three-necked flask, cool to...

Embodiment 2

[0041] This embodiment provides a methylprednisolone intermediate and a preparation method thereof. The preparation method comprises the steps of:

[0042] (1) Dechlorination reaction: add 350ml of butanone, 50g of the compound shown in formula I, 20g of zinc powder, and 75ml (78.7g) of glacial acetic acid into the three-necked flask, and heat up to 50-55°C for 6-7h; TLC Track the reaction. After the reaction is finished, cool the system down to below 35°C, add 350ml of dichloromethane, filter, and wash the filter cake with a small amount of dichloromethane; steam the filtrate to a paste, add 250ml of water, stir at room temperature for 1h, pump Filter, wash with water to neutrality, dry to obtain the compound shown in 43.5g formula II, the yield of the compound shown in formula II is 96.1%, and purity is 95.2% (HPLC);

[0043] (2) Bromination reaction: Add 400ml of acetone and 20ml of water into a 1L three-necked flask, cool to -5 ~ 0°C, add 20g of fluoboric acid, pass in ni...

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Abstract

The invention discloses a methylprednisolone intermediate debrominated product and a preparation method thereof. According to the preparation method, a compound shown as a formula I is used as a raw material, and a dechlorination reaction, a bromination reaction, a debromination reaction and an oxidation reaction are sequentially performed to prepare a compound (debrominated substance) shown as aformula V. The preparation method has the advantages of short synthetic route, high yield, low cost and easily available raw materials, is suitable for industrial production, and has very high industrial value.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and in particular relates to a debrominated methylprednisolone intermediate and a preparation method thereof. Background technique [0002] Methylprednisolone has strong anti-inflammatory effect and weak sodium retention effect, and its anti-inflammatory effect is 7 times that of cortisone. Methylprednisolone is a medium-acting glucocorticoid, and its effect is similar to that of prednisolone. Its anti-inflammatory effect is 3 times that of prednisolone, and its glucose metabolism is 10 times stronger than that of hydrocortisone. The retention effect is weak, and there is no side effect of potassium excretion. Due to its powerful anti-inflammatory, immunosuppressive, anti-allergic, anti-shock and other pharmacological effects, methylprednisolone is widely used clinically in respiratory diseases, endocrine disorders, rheumatic diseases, collagen diseases, blood diseases, skin diseases, Neurolog...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/0045Y02P20/55
Inventor 谢祚宜刘喜荣曾春玲
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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