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Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material

A synthetic method, the technology of methylpregnant, which is applied in the field of steroidal compound synthesis, can solve the problems of poor selective reduction, poor purification of products, high cost, etc., and achieves environmental protection process, high yield and low production cost Effect

Active Publication Date: 2021-11-16
王涛
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  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This synthesis technology uses stigmasterol as a raw material to synthesize cholesterol. In the hydrogenation reaction, a palladium carbon catalyst is used, which has high cost, poor selective reduction, difficult purification of the product, and low yield.

Method used

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  • Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material
  • Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material
  • Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material

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Embodiment 1

[0040] Cholesterol synthesis method, as attached figure 1 shown, including the following steps:

[0041] 1 Etherification reaction: In a 500ml three-necked flask, put 20g of 4-BA, 70ml of absolute ethanol, 120mg of phosphotungstic acid, stir, add 16ml of triethyl orthoformate, stir for 4 hours at room temperature, and pour 400ml of sodium bicarbonate solution after the reaction 21-hydroxy-20-methylpregna-3-ethoxy-3,5-diene 21g was obtained by filtering, beating with 80ml of petroleum ether, and drying under reduced pressure. The molar yield is 97%.

[0042] 2 Oxidation reaction: In a 500ml three-necked flask, put 21g of 21-hydroxy-20-methylpregna-3-ethoxy-3,5-diene, 100ml of DMSO, cool down to 0-10℃ in ice water, add triethylamine 56.2ml, add 32.8g sulfur trioxide pyridinium salt in batches, stir and react at room temperature for 3h, pour into 500ml ice water after reaction, extract with ethyl acetate, wash with water, wash with brine, dry and concentrate to obtain 3-ethoxy-...

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Abstract

The invention provides a method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone (4-BA) as a raw material. The method comprises the step of: (1) carrying out etherification reaction, oxidation reaction, Grignard reagent addition reaction, sulfonylation reaction, reduction reaction, acetylation reaction and reduction reaction on 4-BA and triethyl orthoformate to obtain cholesterol. The synthesis method is simple in process, high in yield, low in cost, environment-friendly in process and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing steroid compounds, in particular to a method for synthesizing cholesterol. Background technique [0002] Cholesterol, also known as cholesterol, is a derivative of cyclopentane polyhydrophenanthrene, widely present in animals. It is an indispensable and important substance for animal tissue cells. It is not only involved in the formation of cell membranes, but also a raw material for the synthesis of bile acids, vitamin D and steroid hormones. [0003] At present, the source of cholesterol is animals, mainly after saponifying the brains and spinal tendons of pigs, cattle, and sheep, and then extracting them with organic solvents. Since many diseases found now are transmitted from animals to humans, especially the emergence of mad cow disease in Europe at the end of the last century, and the infection of Streptococcus suis at the beginning of this century, people have doubts about the safety of choles...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/00Y02P20/55
Inventor 万定建孟宪志李民强
Owner 王涛
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