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Method for preparing 17alpha-hydroxyl progesterone

The technology of hydroxyprogesterone and hydroxyl group is applied in the field of preparation of 17α-hydroxyprogesterone, which can solve the problems of low yield and the like, and achieve the effects of short route, high safety and easy availability of raw materials

Active Publication Date: 2015-09-23
BAODING BR BIO STEROIDS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Issei N(Issei N,Shinichiro F,Hiroaki U.The Synthesis of the Corticoid Side Chain.I.An Improved Method for the Preparation of 17α-Hydroxyprogesterone rom Androst-4-ene-3,17-dione.Bull.Chem.oc .Jpn., 1985,58:978-980) etc. have disclosed that using androst-4-ene-3,17-dione as a raw material, a specific regioselective or stereoselective addition of 17-ketone is carried out in the first step In the second step, under TSOH, use trimethyl orthoformate in ethylene glycol to protect the carbonyl and hydroxyl groups, and then carry out iodomethane reaction and other treatments to obtain the 17β-cyano-17-α-hydroxyl compound (2a) Hydration rearrangement under acidic conditions synthesizes 17α-hydroxyprogesterone (6), and the yield of this synthesis method is low, only 69%

Method used

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  • Method for preparing 17alpha-hydroxyl progesterone
  • Method for preparing 17alpha-hydroxyl progesterone
  • Method for preparing 17alpha-hydroxyl progesterone

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Anhydrous methanol (25.0mL) and 4-AD (11.50g) were dropped into the dried reactor (the reactor was blown dry with nitrogen) and stirred, trimethyl orthoformate (6.80g) and PTS (0.187g) were added, and the temperature was 40° C. Stir and keep for 4h, sampling point plate [developing solvent=ethyl acetate / petroleum ether (EA / PE)=2.5 / 1] without raw material, then drop to room temperature, add triethylamine to neutralize pH=7, cool down to -5°C, Stir for 1 h, filter, rinse with an appropriate amount of cold methanol and dry to obtain 3-methoxyandrost-3,5-dien-17 ketone.

[0028] Potassium hydroxide and calcium carbide were ground into powders with a mixer respectively, and sieved through a 50-mesh sieve for use. Potassium hydroxide (7.75g), calcium carbide (21.00g), tert-butanol (24.5mL) and ethylenediamine (65.0 mL) was added to a 500g reaction flask, kept at 40°C for 16h, cooled to 25°C, added 3-methoxyandrost-3,5-dien-17 ketone (11.80g), stirred for 5h, and slowly added ...

Embodiment 2

[0034] Anhydrous ethanol (25.0mL) and 4-AD (11.00g) were dropped into the dried reactor (the reactor was blown dry with nitrogen) and stirred, and triethyl orthoformate (7.80g) and PTS (0.187g) were added at 40° C. Stir and hold for 4h, the sampling point plate (developer=EA / PE=2.5 / 1) is free of raw materials and then cooled to room temperature, add triethylamine to neutralize pH=7, cool down to -5°C, stir for 1h, filter, and cool methanol appropriately Rinse and dry to obtain 3-ethoxyandrost-3,5-dien-17 ketone.

[0035] Potassium hydroxide and calcium carbide were ground into powders with a mixer, respectively, and passed through an 80-mesh sieve for use. Potassium hydroxide (7.75g), calcium carbide (21.00g), tert-butanol (24.5mL) and ethylenediamine (65.0 mL) into a 500g reaction flask, kept at 40°C for 16h, cooled to 25°C, added 3-ethoxyandrost-3,5-dien-17 ketone (11.80g), stirred for 5h, and slowly added dropwise under nitrogen protection. Acetic acid (54.5mL), water (300...

Embodiment 3

[0037] Anhydrous methanol (25.0mL) and 4-AD (10.00g) were put into the dried reaction kettle (the reaction kettle was blown dry with nitrogen) and stirred, trimethyl orthoformate (6.80g) and PTS (0.187g) were added, and the temperature was 40° C. Stir and hold for 4h, the sampling point plate (developer=EA / PE=2.5 / 1) is free of raw materials and then cooled to room temperature, add triethylamine to neutralize pH=7, cool down to -5°C, stir for 1h, filter, and cool methanol appropriately Rinse and dry to obtain 3-methoxyandrost-3,5-dien-17 ketone.

[0038] Grind sodium hydroxide and calcium carbide into powders with a mixer, respectively, and pass through a 50-mesh sieve for later use. Mix sodium hydroxide (5.85g), calcium carbide (21.00g), propanol (19.6mL) and diethylamine (70.0mL) ) into a 500g reaction flask, kept at 40°C for 16h, cooled to 25°C, added 3-methoxyandrost-3,5-dien-17 ketone and stirred for 5h, under nitrogen protection, slowly added dropwise acetic acid, water, ...

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Abstract

The invention relates to a method for preparing 17alpha-hydroxyl progesterone. The method comprises the following steps: a, protecting 3-carbonyl group of 4-androstenedione through ortho formate to obtain etherate; b, enabling reaction between calcium carbide, lower alcohol and strong alkali under the organic alkali condition, adding the etherate obtained in the step a, and enabling reaction to obtain 17beta-alkynyl-17alpha-hydroxyl substitute; c, conducting hydration rearrangement on the 17beta-alkynyl-17alpha-hydroxyl substitute under the acidic condition to obtain the 17alpha-hydroxyl progesterone; d, purifying the product obtained in the step c. According to the method, 4-androstenedione is used as substrate to prepare the 17alpha-hydroxyl progesterone through three steps of reaction of etherification, ethynylation and hydrolysis, and the total yield can reach 88% or above.

Description

technical field [0001] The invention relates to a method for preparing 17α-hydroxyprogesterone, in particular to a method for producing 17α-hydroxyprogesterone by using 4-androstenedione as a starting material. Background technique [0002] Before the 1960s, my country had always been a major importer of steroid drug intermediates. From Huang Minglong, domestic diosgenin and turmeric were used as starting materials, and steroids (4-androstenedione, 17α-hydroxylutein) were produced by diene. ketone, cortisone acetate), and gradually transformed from a big importer to a big exporter. In the 21st century, due to the development of the paper industry and the oil and fat industry, a large amount of by-product phytosterols has accumulated in the world. The present invention describes a method for producing 17α-hydroxyprogesterone from 4-androstenedione. [0003] At present, the domestic production of 17α-hydroxyprogesterone mainly uses gasoline to extract saponin from turmeric, a...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/004
Inventor 李超余伟
Owner BAODING BR BIO STEROIDS CO LTD
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