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Preparation method of DHEA (dehydroepiandrosterone) intermediate 3 beta- acetoxyl- androstane-3, 5- diene-17-ketone

A technology of acetoxy, 1.DHEA, applied in the direction of steroids, organic chemistry, etc., can solve the problems of high treatment cost, difficult wastewater treatment, and difficult material quality control, so as to reduce production costs, high purity, and high-quality products Quality stable and reliable effect

Active Publication Date: 2014-04-02
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If washing water is considered, the proportion of waste water exceeds 60 times. From the perspective of industrialization, waste water is difficult to treat and the treatment cost is high.
At the same time, wet materials are sensitive to temperature, and need to be vacuum-baked below 40°C. The production efficiency is low and it is difficult to control the quality of materials.

Method used

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  • Preparation method of DHEA (dehydroepiandrosterone) intermediate 3 beta- acetoxyl- androstane-3, 5- diene-17-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 500ml three-necked flask, add 50g 4AD and 250ml chloroform, stir and dissolve at room temperature, then add 2.5g 48% hydrobromic acid, slowly raise the temperature to 55-60°C; add 40ml isopropenyl acetate dropwise, about 4-5 Hours of dripping, after dripping, reflux reaction for 1 to 1.5 hours, TLC detection of the reaction end point; after the reaction, add 3ml of triethylamine to neutralize, make the pH value about 7, atmospheric distillation for about 0.5 to 1 hour, recover 90~ 95% chloroform, changed to reduced pressure distillation until evaporated to dryness; added 50 ml of methanol, stirred evenly, cooled to -5 ~ 0°C, allowed to stand for crystallization for 2 to 3 hours, filtered with suction, washed the filter cake with a small amount of cold methanol, and dried Dry to obtain 57.2g of the intermediate product, the HPLC content reaches 99.4%, and the weight yield is 114.4%.

Embodiment 2

[0018] In a 500ml three-neck flask, add 50g 4AD and 400ml toluene, stir and dissolve at room temperature, then add 0.5g p-toluenesulfonic acid, slowly raise the temperature to 55-60°C; add 40ml isopropenyl acetate dropwise, drop for about 4-5 hours Finished, after dropping, reflux reaction for 1 to 1.5 hours, TLC to detect the reaction end point; after the reaction, add 1ml triethylamine to neutralize, make the pH value about 7, then recover toluene by vacuum distillation, evaporate to complete dryness, stop distillation Add 50 ml of methanol, stir well, cool down to -5~0°C, let stand for crystallization for 2~3 hours, filter with suction, wash the filter cake with a small amount of cold methanol, and dry to obtain 56.5g of product, HPLC content≥99.2%, The weight yield is 113%.

Embodiment 3

[0020] In a 500ml three-neck flask, add 50g 4AD and 400ml ethyl acetate, stir to dissolve at room temperature, then add 2ml 50%H 2 SO 4 , slowly raise the temperature to 55-60°C; add 40ml of isopropenyl acetate dropwise, and drop it in about 4-5 hours. Neutralize with triethylamine to make the pH value about 7, then distill under reduced pressure to recover ethyl acetate, evaporate to complete dryness, stop distillation; add 50 ml of methanol, stir well, cool to -5 ~ 0°C, and stand for crystallization for 2 ~3 hours, suction filtration, washing the filter cake with a small amount of cold methanol, and drying to obtain 55.2 g of product, HPLC content ≥ 99.5%, weight yield 110.4%.

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Abstract

The invention discloses a preparation method of DHEA (dehydroepiandrosterone) intermediate 3 beta-acetoxyl-androstane-3,5-diene-17-ketone. The preparation method is characterized in that esterification reaction reagent is isopropenyl acetate. The preparation method comprise the following steps of dissolving 1W of 4AD (4-androstenediol) into 3-8V of organic solvent, wherein W is weight g, and V is volume ml; adding 1-5w% strong acidic catalyst, stirring and heating up to the reaction temperature of 40-80 DEG C; dripping 0.5-1.2 V of isopropenyl acetate, preserving heat and reacting for 1-2 hours after dripping, until displaying completion of reaction of raw materials by TLC (Thin Layer Chromatography); adding 2-6% V triethylamine for neutralization after reaction, and concentrating the solvent to dry; adding 1V of methyl alcohol, dissolving while stirring, cooling to crystallize for 2-3 hours, filtering, performing solvent washing, and baking to dry below 70 DEG C, thereby obtaining the DHEA intermediate 3 beta- acetoxyl- androstane-3, 5- diene-17-ketone. The DHEA intermediate prepared by the invention has high yield, high purity and steady mass, and can be baked under normal pressure; more importantly, solvent recovery rate is high, and the preparation method almost produces no wastewater, is economic and environmental friendly, and is very beneficial to industrial production.

Description

technical field [0001] The invention belongs to a preparation method of a steroid hormone drug intermediate, in particular to a preparation method of a dehydroepiandrosterone (DHEA) intermediate 3β-acetyloxy-androsta-3,5-dien-17-one. Background technique [0002] DHEA is an important active substance secreted by the human endocrine system to regulate the normal physical and sexual functions of the human body and prolong the physiological and psychological life of the human body. Human endocrine disorders, or as the age increases, the secretion decreases, and it must be supplemented in vitro. Therefore, DHEA is very popular in the world as a nutritional health product for middle-aged and elderly people. At the same time, it is also an indispensable main raw material for the production of a large number of drugs such as sex hormone drugs, hormonal muscle relaxant drugs, and family planning drugs, and has a broad market prospect. [0003] The traditional production process of...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 甘红星胡爱国羊向新张竟成
Owner HUNAN KEREY BIOTECH
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