Preparation method of 17,21-dihydroxy steroid derivative

A technology of bishydroxysteroid and steroid enol silyl ether, which is applied in the field of preparation of 17,21-bishydroxysteroid derivatives, can solve the problems of no literature report and the like, achieves simple operation, high yield and easy industrialization Effect

Active Publication Date: 2015-10-14
TIANJIN JINYAO GRP
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  • Summary
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the enol silyl ether compound I shown in the following formula is the method for preparing the c

Method used

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  • Preparation method of 17,21-dihydroxy steroid derivative
  • Preparation method of 17,21-dihydroxy steroid derivative
  • Preparation method of 17,21-dihydroxy steroid derivative

Examples

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Embodiment 1

[0049] Example 1 Preparation of 17,21-dihydroxy compound AIII with enol silicon ether compound AI as starting material

Embodiment 1-1

[0051] Take compound AI (100g, 0.23mol) and dissolve it in 1L dichloromethane solution; take mCPBA (85%, 162.4g, 0.8mol) and dissolve it in 3.25L dichloromethane solution and add powdery dry KHCO 3 (70g, 0.7mol); combine mCPBA and KHCO 3 The mixed solution was added to the dichloromethane solution of compound AI cooled to 0°C in 1 hour. The temperature of the reaction system was controlled to 0~5°C, and the reaction system was stirred while adding. Thin layer chromatography was used to monitor the progress of the reaction. After the reaction is complete, add an appropriate amount of 10% sodium thiosulfate aqueous solution to remove the excess mCPBA, use starch potassium iodide test paper to test the non-oxidation of the reaction solution, add 1L water, separate the layers, separate the organic layer, and use 1L dichloromethane for the water layer Extract once, combine the organic layers and wash with water to neutrality, concentrate and nearly dry to obtain crude AII. The crude A...

Embodiment 1-2

[0053] Take compound AI (100g, 0.23mol) and dissolve it in 1L dichloromethane solution; take mCPBA (85%, 162.4g, 0.8mol) and dissolve it in 3.25L dichloromethane solution and add powdered dry KHCO3 (70g, 0.7mol) ); put mCPBA and KHCO 3 The mixed solution was added to the dichloromethane solution of compound AI cooled to 10°C within 1 hour, and the temperature of the reaction system was controlled to 10°C±2°C. Stirring while adding, the progress of the reaction was monitored by thin layer chromatography After the reaction is complete, add an appropriate amount of 10% sodium thiosulfate aqueous solution to remove excess mCPBA, use starch potassium iodide test paper to test the non-oxidation of the reaction solution, add 1L of water, separate the layers, separate the organic layer, and use 1L of dichloride for the water layer. Methane was extracted once, the combined organic layer was washed with water to neutrality, concentrated to near dryness to obtain crude AII. The crude AII o...

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Abstract

The invention relates to a method for preparing a 17,21-dihydroxy steroid compound by taking a steroid silyl enol ether compound I as an initiator.

Description

technical field [0001] This patent relates to a preparation method of 17,21-dihydroxy steroid derivatives. Background technique [0002] 17,21-dihydroxyl is an important functional group of steroidal compounds, and many steroidal compounds have the structure of 17,21-dihydroxyl or the corresponding ester, such as: dexamethasone, diflumethasone, betamethasone, prednisolone , prednisone, halometasone, methylprednisolone, aclomethasone, paramethasone, methylprednisolone acetate, loteprednol etabonate, etc. Therefore, the preparation of steroidal 17,21-dihydroxy compounds is very important. [0003] The document "J.Org.Chem.1986,51,4323-4325" reported that at 0°C, a dichloromethane solution of m-chloroperoxybenzoic acid (mCPBA, 3 equivalents) was slowly added dropwise to a steroid enol silicon Ether 14 (1 equiv) and KHCO 3 (Excessive) dichloromethane mixed solution, reacted for 1.5 hours, and then added 1N HCL / THF solution, a solid was precipitated, and the product cortisone ...

Claims

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Application Information

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IPC IPC(8): C07J5/00C07J21/00
CPCC07J5/0076C07J21/00C07J71/0015
Inventor 卢彦昌张杰王淑丽
Owner TIANJIN JINYAO GRP
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