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Preparation method for 17a,21-dyhydroxy progesterone

A technology of progesterone and dihydroxy, which is applied in the field of organic compound preparation, can solve the problems of complex preparation process, poor reproducibility and high cost, and achieve the effect of high yield, low cost and good reproducibility

Active Publication Date: 2012-07-04
河北远大九孚生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 17a, 21-dihydroxyprogesterone is an important intermediate of corticosteroids. It is prepared by microbial methods in the prior art. This preparation method has defects such as complicated preparation process, poor reproducibility, high cost and low yield.

Method used

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  • Preparation method for 17a,21-dyhydroxy progesterone
  • Preparation method for 17a,21-dyhydroxy progesterone
  • Preparation method for 17a,21-dyhydroxy progesterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of 3-ethoxy-17a-hydroxy-20-(arimino)-21-benzyloxyprogesterone.

[0029] First prepare 3-ethoxyandrost-3,5-dien-17-one:

[0030] Add 10g of androst-4-ene-3,17-dione and 10ml of absolute ethanol into the reaction flask, add 0.1g of p-toluenesulfonic acid and 10ml of triethyl orthoformate under stirring, heat up to 40°C and keep for 3 hours to get. Melting point 145 to 146°C.

[0031] Then prepare 3-ethoxyl-17a-hydroxyl-20-(arimino)-21-benzyloxyprogesterone: under the protection of nitrogen gas into the reactor, the tetrahydrofuran solution of 0.1mol / L samarium diiodide 15L was added to the reactor, under stirring, 56g of 2,6-dimethylbenzene isonitrile and 700ml of hexamethylphosphoric triamide were added, cooled to -15°C with cold brine, and 117.5g of benzyloxymethyl chloride was added dropwise After the addition, stir at this temperature for 3 hours, then add 78.5g of 3-ethoxyandrost-3,5-dien-17-one, react at 0°C to 3°C for 14 hours, and confirm the re...

Embodiment 2

[0041] This example uses the 3-ethoxyandrost-3,5-dien-17-one prepared in Example 1.

[0042](1) Preparation of 3-ethoxyl-17a-hydroxyl-20-(arimino)-21-benzyloxyprogesterone: under the protection of nitrogen gas into the reactor, 0.1mol / L samarium diiodide Add 15L of tetrahydrofuran solution into the reactor, under stirring, add 50g of 2,6-dimethylbenzene isonitrile and 700ml of hexamethylphosphoric triamide, cool to -15°C with cold brine, add benzyloxymethyl chloride dropwise 110g, after adding, stir at this temperature for 3 hours, then add 70g of 3-ethoxyandrost-3,5-dien-17-one, react at 0℃~3℃ for 14 hours, confirm the reaction by thin layer chromatography End point (composition of developing agent: n-hexane:ethyl acetate=5:5), when the raw material spots disappear, the reaction ends. Then add a small amount of water and 3L of n-hexane to stir and filter, the filtrate is allowed to stand for stratification, and the organic layer is distilled off the solvent under reduced pre...

Embodiment 3

[0052] This example uses the 3-ethoxyandrost-3,5-dien-17-one prepared in Example 1.

[0053] (1) Preparation of 3-ethoxyl-17a-hydroxyl-20-(arimino)-21-benzyloxyprogesterone: under the protection of nitrogen gas into the reactor, 0.1mol / L samarium diiodide Add 15L of tetrahydrofuran solution into the reactor, under stirring, add 60g of 2,6-dimethylbenzene isonitrile and 700ml of hexamethylphosphoric triamide, cool to -15°C with cold brine, add benzyloxymethyl chloride dropwise 130g, after adding, stir at this temperature for 3 hours, then add 80g of 3-ethoxyandrost-3,5-dien-17-one, react at 0℃~3℃ for 14 hours, confirm the reaction by thin layer chromatography End point (composition of developing agent: n-hexane:ethyl acetate=5:5), when the raw material spots disappear, the reaction ends. Then add a small amount of water and 3L of n-hexane to stir and filter, the filtrate is allowed to stand for stratification, and the organic layer is distilled off the solvent under reduced pr...

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Abstract

The invention discloses a preparation method for preparing 17a,21-dyhydroxy progesterone, which comprises the following three steps of reaction: 2,6-dimethyl benzyl cyanide, benzoyl methyl chloride and 3-ethyoxyl androstane-3,5-diene-17-ketone are used for preparing 3-ethyoxyl-17a-hydroxyl-20-(epi-arylimino)-21-benzoyl progesterone; hydrolyzing the 3-ethyoxyl-17a-hydroxyl-20-(epi-arylimino)-21-benzoyl progesterone obtained in step (1) to obtain 17a-hydroxyl-21-benzoyl progesterone; and hydrogenizing and removing benzyl from the 17a-hydroxyl-21-benzoyl progesterone obtained in step (2) to obtain the 17a,21-dyhydroxy progesterone. The 17a,21-dyhydroxy progesterone prepared with the method has the advantages of easily-controlled technical condition, good reproducibility, low cost and high yield.

Description

technical field [0001] The invention relates to the technical field of organic compound preparation, in particular to a preparation method of 17a, 21-dihydroxyprogesterone. Background technique [0002] 17a, 21-dihydroxyprogesterone is an important intermediate of corticosteroids. It is prepared by microbial methods in the prior art. This preparation method has defects such as complicated preparation process, poor reproducibility, high cost and low yield. Contents of the invention [0003] In order to solve the defects in the process of preparing 17a, 21-dihydroxyprogesterone by microbial method, the present invention provides a method for preparing 17a, 21-dihydroxyprogesterone with good reproducibility, low cost and easy process control. [0004] The present invention is achieved in this way: the preparation method of 17a, 21-dihydroxyprogesterone is characterized in that the synthetic route is: [0005] (1) Utilize 2,6-dimethylbenzene isonitrile, benzyloxymethyl chlori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
Inventor 赵云现
Owner 河北远大九孚生物科技有限公司
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