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Dehalogenation methodof 9-halogenated steroid compound and application

A technology of steroidal compounds and compounds, applied in the direction of steroidal compounds, organic chemistry, etc., can solve problems affecting normal production of products, high cost of environmental protection treatment, environmental pollution, etc., achieve simple and easy synthesis process, improve production applicability, highly operable effect

Pending Publication Date: 2020-12-29
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the above-mentioned processes use heavy metal raw materials, highly toxic raw materials, etc., causing serious pollution to the environment, high cost of environmental protection treatment or use of restricted raw materials; thus limiting the normal application of this type of reaction, and affecting the normal production of this type of product

Method used

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  • Dehalogenation methodof 9-halogenated steroid compound and application
  • Dehalogenation methodof 9-halogenated steroid compound and application
  • Dehalogenation methodof 9-halogenated steroid compound and application

Examples

Experimental program
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Effect test

Embodiment 1

[0141]

[0142] Add 200mL of 75% ethanol, 9.8g of potassium carbonate, 11mL of 50% aqueous hypophosphorous acid, 20g of compound I-1 and 4.3g of AIBI to the reaction flask in turn at room temperature, heat up to 70°C for reaction, TLC until there is no raw material, and post-treatment to precipitate a solid , filtered, and dried to obtain 15.2 g of compound II-1 as a solid, with a yield of 92.3% and a purity of 96.8%.

Embodiment 2

[0144]

[0145] Add 200mL 2-methyltetrahydrofuran, 9g sodium carbonate, 9.9mL 50% hypophosphorous acid aqueous solution, 20g compound I-2 and 3.3g AIBA to the reaction flask successively at room temperature, heat up to 65°C for reaction, TLC until there is no raw material, post-treatment The solid was precipitated, filtered, and dried to obtain 15.2 g of compound II-2 as a solid, with a yield of 91.5% and a purity of 96.5%.

Embodiment 3

[0147]

[0148] Add 160mL of n-butanol, 13mL of 33% sodium hydroxide solution, 9.9mL of 50% hypophosphorous acid aqueous solution, 20g of compound I-3 and 2.5g of CABN into the reaction flask successively at room temperature, raise the temperature to 80°C for reaction, TLC until there is no raw material, After post-treatment, a solid was precipitated, filtered, and dried to obtain 15.3 g of compound II-3 as a solid, with a yield of 93.4% and a purity of 97.0%.

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Abstract

The invention provides a dehalogenation method of a 9-halogenated steroid compound and application, and relates to the technical field of chemical synthesis. The dehalogenation method of the 9-halogenated steroid compound comprises the following steps: reacting a compound I with a hydrogen donor and an azo radical initiator to obtain a 9-dehalogenated product compound II of the 9-halogenated steroid compound. According to the dehalogenation method of the 9-halogenated steroid compound, a hydrogen donor adopts one or a combination of more of hypophosphorous acid and hypophosphite, formic acid and formate, organic silicon hydride, hydrazine compounds or cyclohexene, and an initiator adopts an azo free radical initiator. Reagents such as chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride which are high in toxicity and cause serious pollution to the environment are not used in the reaction, the method is green and environmentally friendly, the synthesis process is simple, convenient and easy to implement, and the production applicability is improved.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a dehalogenation method and application of a 9-halogenated steroid compound. Background technique [0002] Corticosteroids have various pharmacological effects such as anti-inflammation, anti-allergy, anti-shock and immunosuppression, so corticosteroids are widely used in the treatment of skin diseases. The key step in the chemical synthesis method of this class of drugs is the dehalogenation reaction of 9-halogenated steroidal compounds. The more conventional dehalogenation method in the prior art is to add 9-halogenated steroids into a solvent, and react with chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride at a certain temperature to form a dehalogenation product. Most of the above-mentioned processes use heavy metal raw materials, highly toxic raw materials, etc., causing serious pollution to the environment, high cost of environmen...

Claims

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Application Information

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IPC IPC(8): C07J5/00C07J7/00C07J71/00
CPCC07J5/0053C07J5/0076C07J5/0092C07J7/0045C07J7/002C07J71/001C07J71/0031
Inventor 王亚江刘志友张彦巧杨娣陈伟徐珲
Owner TIANJIN PHARMA GROUP CORP
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