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Preparation method of progesterone

A technology of progesterone and acidic ionic liquid, which is applied in the field of progesterone preparation, can solve the problems of poor safety, difficulty, and heavy pollution, and achieve the effect of strong designability and low green pollution

Active Publication Date: 2021-04-23
湖北共同甾体药物研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many production methods of progesterone. When natural plants are used as raw materials for preparation, it is difficult to meet the needs of domestic and foreign markets due to the soaring price of raw materials. The use of chemical synthesis methods to prepare progesterone has gradually attracted close attention from domestic and foreign manufacturers.
[0003] At present, there have been many reports on the synthesis of progesterone, but there are problems such as complex process, high difficulty, heavy pollution, poor safety, and high cost, which restrict the development of progesterone preparation technology.

Method used

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  • Preparation method of progesterone
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preparation example Construction

[0037] In one embodiment, a method for preparing an acidic controllable ionic liquid catalyst is proposed, which specifically includes the following steps:

[0038] (1) 1,3-propane sultone and organic amine are used as raw materials, and ethyl acetate is used as a solvent, wherein the molar ratio of 1,3-propane sultone and organic amine is 1 to 4:1, The organic amine is added dropwise under the condition of stirring in a water bath, the reaction temperature is 40-80°C, and the stirring time is 1-3 hours. After the reaction, the ionic liquid intermediate can be obtained after filtration, washing and vacuum drying. The organic amine in this step is selected from hexamethylenetetramine, pyridine, N,N-carbonylimidazole, triethylamine, N - Methylimidazole, tributylamine, piperidine, quinoline, pyrazine and indole.

[0039] (2) Taking the ionic liquid intermediate, concentrated sulfuric acid or concentrated hydrochloric acid prepared in step (1) as raw material, water as solvent, w...

Embodiment 1

[0043] In this embodiment, tetrapropanesulfonic acid base hexamethylenetetramine tetrasulfate copper salt (abbreviated as ([TshxH][(1 / 2Cu 2+ ) SO 4 2- ] 4 )) as an example, the preparation method of catalyst is as follows:

[0044] (1) Weigh 0.4mol of 1,3-propane sultone and 100mL of ethyl acetate into a 250mL three-neck flask, add 0.1mol of hexamethylenetetramine dropwise, and stir at 70°C for 2h. After the reaction, the ionic liquid intermediate tetrapropanesulfonate hexamethylenetetramine salt (abbreviated as (Tshx)) can be obtained after filtration, washing and vacuum drying.

[0045] (2) Dissolve the precursor 0.1mol Tshx (prepared in step (1)) in 60mL water at room temperature, add 0.4mol concentrated sulfuric acid dropwise, and react at a constant temperature of 90°C for 3h. After the reaction finishes, after drying, washing, and vacuum drying, yellow viscous liquid tetrapropanesulfonic acid base hexamethylenetetramine tetrahydrosulfate (abbreviated as ([TshxH][HSO ...

Embodiment 2

[0055] In order to verify the catalytic effects of different types of catalysts, in this embodiment, 20 g of raw materials (20S)-20-hydroxymethylpregn-4-en-3-one, solvent N,N- Dimethylformamide (DMF) 100mL and catalyst 1.2g were rapidly stirred at 40°C for 6h.

[0056] At the end of the reaction, the catalyst and the reaction system were separated into layers, and the catalyst was washed with ethyl acetate, dried in vacuum, and applied mechanically again. Take the upper organic layer and distill under normal pressure, distill off the fraction below 200°C, add water to precipitate the solid after cooling, filter to obtain the crude progesterone, and recrystallize to obtain the fine progesterone.

[0057] Different types of catalysts prepared in Example 1 were selected, and the method for producing progesterone catalyzed by an acidic controllable ionic liquid catalyst proposed in this example was used to carry out an example operation, and the results of the oxidative decarbonyl...

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Abstract

The invention discloses a preparation method of progesterone, which comprises the following steps of taking (20S)-20-hydroxymethyl pregna-4-ene-3-ketone as a raw material, and an acidic ionic liquid-based catalyst as a catalyst to react in a solvent, after the reaction is finished, separating the catalyst to obtain a reaction solution, sequentially concentrating the obtained reaction solution under normal pressure, adding water to separate out solid, filtering to obtain a progesterone crude product, and recrystallizing to obtain a progesterone fine product. The catalyst is prepared through catalysis of the acid controllable ionic liquid catalyst, the acid controllable ionic liquid catalyst has the characteristics of being high in designability, small in green pollution and the like, and when the acid controllable ionic liquid catalyst serves as the catalyst, the catalyst and a product are automatically layered after reaction; the catalyst can realize acidity controllability and regeneration through simple treatment after multiple cycles, so that the catalyst has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of progesterone preparation, in particular to a method for preparing progesterone using an acidic controllable ionic liquid as a catalyst. Background technique [0002] Progesterone, also known as progesterone, pregnenedione, and progestin, is a natural progesterone secreted by the corpus luteum of the ovary, and is also the most important progesterone in the pregnane series. Progesterone can promote the maturation and development of uterus and mammary gland, and is an essential substance for maintaining pregnancy. Its structure is pregn-4-ene-3,20-dione. Studies have found that in addition to being used in the field of reproductive health, progesterone can also be used for the treatment of obstetrics and gynecology diseases, intractable ascites, sleep apnea syndrome, chronic respiratory failure and ureteral calculi. At the same time, progesterone is also a key intermediate of steroidal drugs such as cortic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00B01J31/02
CPCB01J31/0285B01J2231/70C07J7/002
Inventor 韩晓祥蔡锦旺寿飞艳杨水芬黄江辉蒋胜筹
Owner 湖北共同甾体药物研究院有限公司
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