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Preparation method of androst-2-ene-17-one

A technology for androsteroid and epiandrosterone, which is applied in the field of steroid drug intermediates, can solve the problems of harsh reaction conditions, low product yield, low purity and the like, and achieves the effects of low production cost, good reaction selectivity and simple operation.

Pending Publication Date: 2021-12-14
YICHENG GOTO PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of preparation method of androst-2-en-17-one in view of the deficiencies in the prior art, in order to solve the problems of harsh reaction conditions, low product yield and low purity in the prior art

Method used

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  • Preparation method of androst-2-ene-17-one

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preparation example Construction

[0023] The preparation method of the androst-2-en-17-one comprises the following steps:

[0024] 1) After mixing epiandrosterone, a halogen-containing compound, a catalyst and a solvent, a halogenation reaction is carried out to obtain compound 1;

[0025] 2) Compound 1, a catalyst and a solvent are mixed for elimination reaction to obtain androst-2-en-17-one.

[0026] The halogen-containing compound in step 1) of the present invention preferably comprises bromosuccinimide, N-bromosuccinimide or carbon tetrachloride.

[0027] The catalyst in step 1) of the present invention is preferably triphenylphosphine; the solvent preferably includes one or more of dichloromethane, acetone, dimethylsulfoxide and N,N-dimethylacetamide; when When the solvent contains several components at the same time, each component is preferably mixed in an equal volume ratio.

[0028] The mass volume ratio of epiandrosterone, halogen-containing compound, catalyst and solvent in step 1) of the present ...

Embodiment 1

[0035] Add 5g of epiandrosterone, 9g of bromosuccinimide and 9g of triphenylphosphine into a reaction kettle filled with 155mL of dichloromethane, mix well, perform halogenation reaction at 45°C for 4h, and confirm the end point of the reaction by TLC. After the reaction was completed, the reaction solution was cooled to room temperature, washed with ethanol solution to remove triphenylphosphine, then washed twice with 100 mL saturated aqueous sodium bicarbonate solution, concentrated under reduced pressure, and dried with anhydrous sodium sulfide to obtain compound 1.

[0036] Mix 6.5g of compound 1, 3g of lithium carbonate and 6g of lithium bromide in 125mL of ethyl acetate, eliminate the reaction at 55°C for 7h, and confirm the end point of the reaction by TLC. After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and washed with a 25% hydrochloric acid solution to remove lithium carbonate and lithium bromide, then washed twice wit...

Embodiment 2

[0039] Add 6.5g of epiandrosterone, 13g of carbon tetrachloride and 11g of triphenylphosphine into a reaction kettle filled with 90mL of acetone and 85mL of dimethyl sulfoxide mixed solvent, mix well, and conduct a halogenation reaction at 55°C for 2h. TLC confirmed the end of the reaction. After the reaction was completed, the reaction liquid was cooled to room temperature, washed with ethanol solution to remove triphenylphosphine, then washed twice with 130 mL saturated aqueous sodium bicarbonate solution, concentrated under reduced pressure, and dried with anhydrous sodium sulfide to obtain compound 1.

[0040] Mix 7.5g of compound 1, 3g of lithium carbonate and 9g of lithium bromide in 145mL of N,N-dimethylacetamide, eliminate the reaction at 65°C for 5h, and confirm the end of the reaction by TLC. After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and washed with a 27% hydrochloric acid solution to remove lithium carbonate an...

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Abstract

The invention belongs to the technical field of steroid drug intermediates. The invention provides a preparation method of androst-2-ene-17-one, which comprises the following steps: 1) mixing epiandrosterone, a halogen-containing compound, a catalyst and a solvent, and performing halogenation reaction to obtain a compound 1; and 2) mixing the compound 1, a catalyst and a solvent, and performing elimination reaction to obtain androst-2-ene-17-one. By reasonably selecting the catalyst and controlling the raw material proportion and process conditions, the yield and purity of the target product are remarkably improved; and moreover, the reaction conditions are mild, the operation is simple, the production cost is low, and the reaction selectivity is good. The yield of the androst-2-ene-17-one prepared by the preparation method is greater than or equal to 94%, and the purity is greater than or equal to 98.5%.

Description

technical field [0001] The invention relates to the technical field of steroid drug intermediates, in particular to a preparation method of androst-2-en-17-one. Background technique [0002] Rocuronium bromide and vecuronium bromide are common muscle-relaxing steroid hormone drugs, which have the advantages of fast onset of action, no accumulation in the body, weak inhibitory effect on the cardiovascular system and small release of histamine, and have become clinically used. An important auxiliary drug for anesthesia in surgical operations. Androst-2-en-17-one is a general intermediate for the production of rocuronium bromide, vecuronium bromide and other muscle-relaxing steroid hormones. The 6-step reaction of enol esterification, double epoxidation, ring opening with different alicyclic amines, reduction, diesterification, bromomethyl amination and other 6-step reactions can obtain different bromamine muscle relaxant steroid drugs, androster- 2-en-17-one occupies an impo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 潘高峰贺一君明小龙
Owner YICHENG GOTO PHARMA
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