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Method for synthesizing 16-dehydropregnenolone by taking dehydropregnenolone acetate as raw material

A technology of pregnant dienolone and diketene acetate, which is applied in the field of synthesis of chemical drugs, can solve problems such as serious side reactions, impact on product quality and yield, and damage, and achieve the effect of less by-products

Inactive Publication Date: 2014-09-03
JIANGSU GRAND XINYI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the traditional process of producing 16-pregnancy dienolone is obtained by dissolving dienolone acetate as raw material in an alcoholic solvent, adding potassium carbonate or sodium hydroxide for reflux hydrolysis, and the disadvantage of this process is the side reaction Seriously, the 16-position double bond of dienolone acetate is destroyed under the action of alcohol solvents and alkalis, which affects product quality and yield

Method used

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  • Method for synthesizing 16-dehydropregnenolone by taking dehydropregnenolone acetate as raw material
  • Method for synthesizing 16-dehydropregnenolone by taking dehydropregnenolone acetate as raw material
  • Method for synthesizing 16-dehydropregnenolone by taking dehydropregnenolone acetate as raw material

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Add 20 grams of dienolone acetate and 200 milliliters of tetrahydrofuran (THF) in the reaction flask, stir for 10 minutes to dissolve;

[0016] Then add 20 milliliters of 20% sodium hydroxide solution to the reaction flask, heat up to 20-30° C., stir the reaction and keep it warm for 1 hour, and then do TLC detection for the reaction. figure 1 A column is the point of contrast dienolone acetate, B column is the result of the spot plate of the reaction solution of this embodiment, B1 is the point of raw material dienolone acetate, and B2 is the product. When TLC detects that dienolone acetate disappears Add 10 ml of hydrochloric acid, adjust the pH to be neutral, raise the temperature to reflux temperature under normal pressure to recover most of the solvent, and recover the remaining solvent by rotary evaporation under reduced pressure; then add 200 ml of water to the residue of rotary evaporation, filter, and wash the filter cake with 100 ml of water , and dried to obt...

Embodiment 2

[0023] Add 10 grams of dienolone acetate to 100 milliliters of N,N-dimethylformamide (DMF) in the reaction flask, stir for 10 minutes to dissolve;

[0024] Add 10 milliliters of 20% sodium hydroxide solution, heat up to 20-30° C., and keep the temperature for 1 hour. After TLC detects that dienolone acetate disappears, add 5 milliliters of hydrochloric acid, and the dot plate diagram and figure 1 The same by-product point was not seen. Adjust the pH to be neutral, recover most of the solvent by raising the temperature under normal pressure, and recover the remaining solvent under reduced pressure; then add 200 ml of water, filter, wash the filter cake with 100 ml of water, and dry to obtain 8.5 g of 16-pregnant dienolone. Yield 91%.

Embodiment 3

[0026] Add 50 grams of dienolone acetate and 500 milliliters of dioxane in the reaction flask, stir and dissolve;

[0027] Add 50 milliliters of 20% sodium hydroxide solution, react at room temperature for 3 hours, TLC detects that dienolone acetate disappears, and the dot plate diagram and figure 1 The same by-product point is not seen, add 25 milliliters of hydrochloric acid, adjust the pH to be neutral, recover most of the solvent by increasing the temperature under normal pressure, and recover the remaining solvent under reduced pressure; then add 400 milliliters of water, filter, wash the filter cake with 100 milliliters of water, and dry to obtain 16-Pregnancy Dienolone 46g. Yield 89%.

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Abstract

The invention discloses a method for synthesizing 16-dehydropregnenolone by taking dehydropregnenolone acetate as a raw material. The method comprises the following steps: dissolving dehydropregnenolone acetate by taking an aprotic solvent as a solvent, adding an aqueous solution of an inorganic base, controlling the reaction temperature to 20-30 DEG C, regulating the pH value to be neutral after the reaction is detected to be finished, raising the temperature to recover the solvent, performing atmospheric distillation and reduced pressure recovery, and adding water for filtering, wherein the filter cake is the 16-dehydropregnenolone. According to the method, protic solvents such as alcohols are avoided, hydrophilic aprotic solvents are used, a few byproducts are produced, and high-purity 16-dehydropregnenolone is obtained.

Description

technical field [0001] The present invention relates to the synthetic method of chemical medicine, particularly a kind of synthetic method of 16-pregnant dienolone Background technique [0002] 16-Pregnant Dienolone is a commonly used pharmaceutical raw material. At present, the traditional process of producing 16-pregnancy dienolone is obtained by dissolving dienolone acetate as raw material in an alcoholic solvent, adding potassium carbonate or sodium hydroxide for reflux hydrolysis, and the disadvantage of this process is the side reaction Seriously, the 16-position double bond of dienolone acetate is destroyed under the action of alcohol solvent and alkali, which affects product quality and yield. The reaction formula is as follows: [0003] Contents of the invention [0004] The purpose of the present invention is to provide an improved method for obtaining 16-pregnant dienolone by hydrolysis of dienolone acetate under alkaline conditions. The inventive method ha...

Claims

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Application Information

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IPC IPC(8): C07J13/00
Inventor 孙玉辉
Owner JIANGSU GRAND XINYI PHARMA
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