Method for preparing 19-nor-4-androstene-3,17-dione

A technology of androstene and diketone, which is applied in the field of chemical preparation, can solve the problems of restricting industrial production, long synthesis route, and long production cycle, and achieve the effects of improving operation safety, short synthesis route and high product quality

Inactive Publication Date: 2017-04-26
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new method uses crude orastone-19. It involves two stages: first making it pure by reacting certain chemical substances together under specific conditions like acidic pH value at different temperatures; second removing impurities that may affect its properties during subsequent processing. Overall this makes up an efficient way to make highly pure products while reducing costs compared to previous methods.

Problems solved by technology

Technological Problem addressed by this patented method involves finding better ways to make certain chemicals that are useful drugs like butyrolactones (BN) without producing unwanted side effects such as excessive hormonal levels caused by other substances found naturally occurring within body fluids called female sex glands.

Method used

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  • Method for preparing 19-nor-4-androstene-3,17-dione
  • Method for preparing 19-nor-4-androstene-3,17-dione
  • Method for preparing 19-nor-4-androstene-3,17-dione

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Embodiment 1

[0041] The first step, hydrolysis reaction: add compound 1 (150g, 1W) and tetrahydrofuran (750ml, 5V) into the three-necked flask, stir to dissolve, control the internal temperature at 20~25°C, prepare 4N HCl (187.5ml, 1.25V), transfer to drop Liquid funnel, drop into the three-necked flask, the temperature during the dropwise addition should not exceed 25°C, after the dropwise addition, keep the reaction at this temperature for 6 hours. Thin layer chromatography (TLC) detects that there is no raw material point, add 2N Na dropwise 2 CO 3 solution (187.5ml, 1.25V), adjust the pH to neutral, concentrate under reduced pressure at 40°C until solvent-free and drip, add ethyl acetate (300ml, 2V) to the aqueous layer to extract twice, combine the organic phases, and wash the organic phases with saturated salt Washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure at 50°C until solvent-free and dripped to obtain hydrolyzate 2 (110 g), with a mola...

Embodiment 2

[0045] The first step, hydrolysis reaction: Add compound 1 (150g, 1W) and ethanol (1500ml, 10V) to the three-necked flask, stir to dissolve, control the internal temperature at -10~-5°C, prepare 6N sulfuric acid (750ml, 5V), and transfer to drop Liquid funnel, drop into the three-necked bottle, the temperature during the dropwise addition should not exceed -10~-5°C, after the dropwise addition, keep the reaction at this temperature for 10 hours. When there is no raw material point detected by TLC, add 6N potassium carbonate solution (750ml, 5V) dropwise, adjust the pH to neutral, concentrate under reduced pressure at 40°C until there is no solvent, add ethyl acetate (1500ml, 10V) to the aqueous layer to extract two Once, the organic phases were combined, and the organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure at 50°C until solvent-free, and dropped to obtain hydrolyzate 2 (105 g), with a molar yield of 91...

Embodiment 3

[0049] The first step, hydrolysis reaction: Add compound 1 (150g, 1W) and methanol (150ml, 1V) to the three-neck flask, stir to dissolve, control the internal temperature at 55~60°C, prepare 0.5N HCl (150ml, 1V), and transfer to the drop solution Funnel, dropwise into the three-necked bottle, the temperature during the dropwise addition should not exceed 55~60°C, after the dropwise addition, keep the reaction at this temperature for 1 hour. When there is no raw material point detected by TLC, add 0.5N potassium hydroxide solution (150ml, 1V) dropwise, adjust the pH to neutral, concentrate under reduced pressure at 40°C until no solvent drops, add ethyl acetate (450ml, 3V) to extract the aqueous layer Twice, the organic phase was combined, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure at 50°C to solvent-free dropwise to obtain hydrolyzate 2 (112g), the molar yield was 97%, HPLC (High Performance Liquid...

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Abstract

The invention discloses a method for preparing 19-nor-4-androstene-3,17-dione. The method comprises the following steps: taking a compound 1 as an initial raw material, carrying out a hydrolysis reaction, a hydrogenation reaction and condensation reaction so as to obtain 19-nor-4-androstene-3,17-dione, wherein the reaction formula is as shown in the specification. According to the method disclosed by the invention, a high-purity 19-nor-4-androstene-3,17-dione product is obtained at the total molar yield of 83% or higher, and the method is low in cost, green, environmental-friendly and suitable for industrial production.

Description

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Claims

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Application Information

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Owner ZHEJIANG XIANJU PHARMA
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