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Preparation method of progesterone

A technology of progesterone and ketal, applied in the direction of steroids, organic chemistry, etc., can solve the problems of operator poisoning, unsuitable for industrialization, and low yield, and achieve the effects of high safety factor, environmental friendliness, and high yield

Pending Publication Date: 2021-07-16
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In this route, highly toxic acetone cyanohydrin is used for hydroxycyanation reaction, which is easy to poison the operator, and the yield is low, so it is not suitable for industrialization

Method used

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  • Preparation method of progesterone
  • Preparation method of progesterone
  • Preparation method of progesterone

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Experimental program
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Effect test

Embodiment 1

[0055] The preparation of embodiment 1 formula 3 compound

[0056]

Embodiment 1-1

[0058] Under the protection of nitrogen, add 50mL dichloromethane, 10g4-AD (compound 2), 2.6mL ethylene glycol, 11.7mL triethyl orthoformate and 0.01g p-toluenesulfonic acid into the reaction flask, react at 20°C, TLC No compound of formula 2 was detected. After the reaction was completed, triethylamine was added to quench the reaction, and concentrated under reduced pressure to 2-3 times the volume. After cooling to room temperature, the concentrate was diluted into ice water, filtered, and dried to obtain 11.3 g of a compound of formula 3 as an off-white solid. Yield 97.9%, HPLC content 97.0%.

Embodiment 1-2

[0060] Under the protection of nitrogen, add 55mL chloroform, 10g4-AD (compound 2), 2.3mL ethylene glycol, 6.5mL trimethyl orthoformate and 0.01g p-toluenesulfonic acid to the reaction flask, react at 25°C, TLC No compound of formula 2 was detected. After the reaction is complete, add pyridine to quench the reaction, concentrate under reduced pressure to 2-3 times the volume, and after cooling down to room temperature, dilute the concentrate into ice water, filter, and dry to obtain 11.2 g of off-white solid formula 3, with a yield of 97.1 %, HPLC content 96.8%.

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Abstract

The invention provides a preparation method of progesterone, and relates to the technical field of chemical synthesis. The preparation method of progesterone comprises the following steps: (a) carrying out condensation reaction on carbonyl on a C3 position of a compound of a formula 2 to obtain a compound of a formula 3 of which the C3 position is ketal; (b) carrying out epoxidation reaction on the carbonyl group on the C17 site of the compound of the formula 3 to obtain a compound of a formula 4 with an epoxy group on the C17 site; and (c) carrying out carbonylation reaction on the epoxy group on the C17 site of the compound shown in the formula 4, and carrying out hydrolysis reaction on the ketal on the C3 site to obtain the compound shown in the formula 1. According to the progesterone preparation method provided by the invention, 4-AD (a compound shown in the formula 2) is used as a starting raw material, and progesterone (a compound shown in the formula 1) is prepared through condensation, epoxidation, carbonylation and hydrolysis reactions. Initial raw materials are easy to obtain, highly toxic chemicals are not needed, the method is environment-friendly, and the safety coefficient is high; and obtained progesterone is high in yield and high in purity, and a process route capable of realizing industrial production is provided.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of progesterone. Background technique [0002] Progesterone (Progesterone), also known as progesterone hormone and luteinizing hormone, is a natural progesterone secreted by the corpus luteum of the ovary. It has a significant morphological effect on the stimulated endometrium in the body. It is necessary to maintain pregnancy and is clinically used in aura. Abortion, habitual abortion, etc. At the same time, progesterone is the key intermediate of steroid drugs such as corticosteroids and androgen. [0003] At present, the traditional process of producing progesterone in industry mainly uses dienolone acetate as raw material to prepare progesterone through hydrogenation, hydrolysis and oxidation reaction. The reaction route is as follows: [0004] [0005] The dienolone acetate used in this route is obtained by extracting diosgenin, which is o...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 徐卫华王亚江
Owner TIANJIN PHARMA GROUP CORP
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