Synthetic method of pregnenolone acetate

A technology of pregnenolone acetate and dienolone acetate, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems of large amount of solvent and small output, and achieve the effects of high selectivity, low cost, and good crystal form

Active Publication Date: 2013-12-18
西安高远生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the catalytic reaction with Raney nickel, the combined yield of hydrohydrolysis is only 85%, and 30 times the volume of ethanol is used as a solvent, and the amount of solvent is relatively large. Under the same equipment conditions, the yield is small

Method used

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  • Synthetic method of pregnenolone acetate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Step 1. Add 750L of ethyl acetate, 100kg of dienolone acetate and 5kg of ammonium acetate to a clean 1000L hydrogenation reactor, and suck in the ethyl acetate mixed solution of palladium / carbon catalyst (0.5kg loading capacity 5 kg) under nitrogen protection. % palladium / carbon catalyst into 50L ethyl acetate), nitrogen replacement 3 times, hydrogen replacement 3 times; the temperature of the reaction kettle was raised to 45°C, the hydrogen pressure was kept at 0.4MPa, and the reaction was stirred for 2 hours, and no ultraviolet absorption was detected by TLC;

[0027] Step 2, filter the reaction solution after the reaction in step 1, transfer the filtered filtrate to the concentration kettle, concentrate and reclaim ethyl acetate at normal pressure until the concentration kettle wall has crystals to separate out, then add 50L mixed solvent in the concentration kettle, The temperature is lowered to below 5° C., and then centrifuged to dry to obtain the crude product of ...

Embodiment 2

[0031] Step 1. Add 850L of ethyl acetate, 100kg of dienolone acetate and 6kg of ammonium acetate to a clean 1000L hydrogenation reactor, and suck in the ethyl acetate mixture of palladium / carbon catalyst (1kg loading capacity 5% The palladium / charcoal catalyst was added to 50L ethyl acetate), nitrogen replacement 5 times, hydrogen replacement 5 times; the temperature of the reaction kettle was raised to 40°C, the hydrogen pressure was kept at 0.6MPa, and the reaction was stirred for 2.5h, and no ultraviolet absorption was detected by TLC;

[0032] Step 2, filter the reaction solution after the reaction in step 1, transfer the filtered filtrate to the concentration kettle, concentrate and reclaim ethyl acetate at normal pressure until the concentration kettle wall has crystals, then add 100L mixed solvent in the concentration kettle, The temperature is lowered to below 5° C., and then centrifuged to dry to obtain the crude product of pregnenolone acetate; the mixed solvent is a ...

Embodiment 3

[0036] Step 1. Add 950L of ethyl acetate, 100kg of dienolone acetate and 7kg of ammonium acetate to a clean 1000L hydrogenation reactor, and suck in the ethyl acetate mixed solution of palladium / carbon catalyst (1.5kg loading capacity 5 kg) under nitrogen protection. % palladium / charcoal catalyst into 50L ethyl acetate), nitrogen replacement 4 times, hydrogen replacement 4 times; the reaction kettle was heated to 35°C, the hydrogen pressure was kept at 0.8MPa, and the reaction was stirred for 3 hours, and no ultraviolet absorption was detected by TLC;

[0037] Step 2, filter the reaction liquid after the reaction in step 1, transfer the filtered filtrate to the concentrated kettle, concentrate and reclaim ethyl acetate at normal pressure until the wall of the concentrated kettle has crystals to separate out, then add 150L mixed solvent in the concentrated kettle, The temperature is lowered to below 5° C. and then centrifuged to dry to obtain the crude product of pregnenolone ac...

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Abstract

The invention discloses a synthetic method of pregnenolone acetate. The method comprises the following steps of: 1, carrying out hydrogenation reaction of dehydropregnenolone acetate at a temperature ranging from 35 to 45 DEG C and under 0.4 MPa to 0.8 MPa by taking ethyl acetate as a solvent and a compound catalyst of a palladium / carbon catalyst and ammonium acetate; 2, filtering the reaction liquid after reaction, concentrating the filtrate under normal pressure, then adding a mixed solvent to the concentrated filtrate, and carrying out centrifugal drying after cooling to obtain crude pregnenolone acetate; 3, washing the crude pregnenolone acetate, then carrying out drip washing by using methanol, and drying to obtain white sandy solid pregnenolone acetate. The synthetic method provided by the invention is mild in reaction conditions; ethyl acetate is used as the solvent, and the solvent is high in recovery and low in dosage; as the palladium / carbon catalyst and ammonium acetate are used as the compound catalyst, the catalytic hydrogenation selectivity is high and no impurity is generated; besides, the aftertreatment is simple and the yield is high; the mass purity of the product can be higher than 99.5%.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a synthesis method of pregnenolone acetate. Background technique [0002] Progesterone is a natural progestin secreted by the corpus luteum of the ovary. It has a significant morphological effect on the estrogen-stimulated endometrium in vivo and is necessary to maintain pregnancy. Pregnenolone acetate is an essential intermediate for the synthesis of progesterone. Because of its complex synthesis equipment and high risk, most progesterone manufacturers mainly purchase pregnenolone acetate required by them. With the reduction and price rise of upstream raw materials such as diosgenin and dienolone acetate, the supply of pregnenolone acetate is becoming increasingly tight. [0003] At present, the process route for synthesizing progesterone from dienolone acetate mainly includes three steps: catalytic hydrogenation, hydrolysis, and Woshi oxid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 史永平
Owner 西安高远生物科技有限公司
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