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Preparation method of dehydropregnenolone acetate

A technology of dienolone acetate and acetic anhydride, which is applied in the direction of steroids and organic chemistry, can solve the problems of oxidant improvement, experiment and production site limitations, and the problem of chromium compound pollution has not been completely solved, and the product yield can be achieved Stable, low cost, less pollution effects

Inactive Publication Date: 2015-12-02
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although this technology has been optimized, the oxidant has not been improved, and the pollution problem caused by chromium compounds has not been completely solved. At the same time, the pressure vessel is used in the first step of the ring opening process, which has certain risks. Experimental and production sites have certain restrictions

Method used

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  • Preparation method of dehydropregnenolone acetate
  • Preparation method of dehydropregnenolone acetate
  • Preparation method of dehydropregnenolone acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A thermometer and a reflux condenser were sequentially installed on a 250ml three-necked flask, and 10g (24.1mmol) of diosgenin, 1.42g (26.5mmol) of ammonium chloride, 150ml of dry acetic anhydride, 0.5ml of pyridine, and a magnetic stirrer were added successively. After plugging with a glass stopper, heat to 90° C. on a collector-type constant temperature heating magnetic stirrer (oil bath) to see that the diosgenin is completely dissolved, and continue to heat up to 140° C. and reflux for 8 hours to stop the reaction. Take the reaction bottle out of the oil bath, cool it down to room temperature naturally and add 40ml of glacial acetic acid, put the reaction bottle into a low-temperature reactor to cool down to about 5°C, slowly drop in the prepared oxidizing solution, keep it warm for 2 hours, and then raise the temperature naturally After reaching room temperature, carry out hydrolysis again, move the reaction bottle into an oil bath, raise the temperature to 100°C, ...

Embodiment 2

[0036] Whole reaction procedure is identical with example 1, and the amount of ammonium chloride in the change experiment process is 1.23g (23.0mmol), and final gained product crude product 6.4g, obtains product 2.12g after recrystallization. The purity is 96.5%, and the yield is 24.7%.

Embodiment 3

[0038] Whole reaction procedure is identical with example 1, and the amount of ammonium chloride in the change experiment process is 1.55g (28.9mmol), and the final gained product crude product 6.8g, obtains product 2.82g after recrystallization. The purity is 94.4%, and the yield is 32.8%.

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Abstract

The invention discloses a preparation method of dehydropregnenolone acetate. The preparation method comprises the following steps: ring opening: taking dioscin as a raw material, taking acetic anhydride as both a reaction reagent and a solvent, adding ammonium chloride and pyridine, carrying out a reaction at 135 to 140 DEG C for 7 to 9 hours, and cooling the obtained reacted liquid naturally to the room temperature; oxidation: adding glacial acetic acid into the cooled reacted liquid, lowering the temperature to 5 to 10 DEG C, dripping an oxidation liquid at the temperature, and holding the temperature after dripping at 5 to 10 DEG C to ensure a reaction for 1.5 to 2.5 hours, wherein the oxidation liquid is a mixture of a catalyst and an oxidant, the catalyst is a compound of oxalic acid and sodium tungstate dihydrate, and the oxidant is 30 wt% hydrogen peroxide; hydrolysis elimination: allowing the temperature of the reacted liquid obtained after oxidation to rise naturally to the room temperature, heating to 95 to 105 DEG C, carrying out backflow for 40 to 50 min, cooling to the room temperature, and carrying out post-treatment. The preparation method has the advantages that the product yield is stable; no grease which is hard to separate is generated during the post-treatment process; as the solvents during the whole reaction process are acetic acid and acetic anhydride, the required equipment is simple, and the pollution as well as the cost is low.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a preparation method of pregnant dienolone acetate. Background technique [0002] Pregnancy Dienolone Acetate (referred to as "diene") is an important intermediate in the synthesis of steroid drugs, which can synthesize most steroid hormone drugs. Its annual output is about 1,000 tons in China. The market The demand is high. Its structural formula is as follows: [0003] [0004] At present, my country's production of dienes mainly uses diosgenin extracted from natural medicines as raw material, and adopts the steroidal saponin degradation method invented by American chemist Marker in the 1940s (Marker: J.Am.Chem.Soc. 1940,62,2537; J.Am.Chem.Soc.1941,63,774; J.Am.Chem.Soc.1947,69,1267.) production, that is, the use of high pressure to open the ring of diosgenin, after chromic anhydride oxidation , finally hydrolyzed to generate dienes to obtain products wit...

Claims

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Application Information

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IPC IPC(8): C07J13/00
Inventor 祝宏吴云龙张俊彭薇
Owner WUHAN INSTITUTE OF TECHNOLOGY
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