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Novel method for synthesizing cholesterol and 25-hydroxycholesterol by taking 22-sterol as raw material

A technology for hydroxycholesterol and cholesterol, applied in the field of steroid synthesis, can solve the problems of inconsistent atom economy, high reaction risk, etc., and achieve the effects of environmental protection, simple reaction process and high yield.

Pending Publication Date: 2022-04-12
王涛
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In this synthetic route, due to the influence of the 3-hydroxyl group, the Grignard reagent Eurolink reaction needs 10 times the Grignard reagent to react, which leads to a very dangerous reaction and does not conform to atom economy.

Method used

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  • Novel method for synthesizing cholesterol and 25-hydroxycholesterol by taking 22-sterol as raw material
  • Novel method for synthesizing cholesterol and 25-hydroxycholesterol by taking 22-sterol as raw material
  • Novel method for synthesizing cholesterol and 25-hydroxycholesterol by taking 22-sterol as raw material

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Experimental program
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Effect test

Embodiment 1

[0040] The synthetic method of cholesterol and 25-hydroxyl cholesterol, as attached figure 1 shown, including the following steps:

[0041] 1. 3-position carbonyl tetrahydropyrrole protection

[0042] Put 1000g of 22-hydroxy-20-methylpregn-4-en-3-one and 5000ml of anhydrous methanol into a 10L three-necked flask, add 200g of tetrahydropyrrole dropwise under heating and reflux, the reaction solution becomes turbid again, and the dropwise addition is completed After the reaction was cooled to room temperature, 1050 g of 22-hydroxy-20-methylpregna-3-tetrahydropyrrole-3,5-diene was obtained by filtration and drying. The molar yield is 90.4%.

[0043] HNMR (500MHz, CDCl3) δ: 5.09(m,1H), 4.78(m,1H), 3.13(m,4H), 1.87(m,4H), 1.04(d,3H), 1.00(d,3H), 0.72(s,3H). Its spectrum is attached figure 2 shown.

[0044] 2, 3 carbonyl glycol protection

[0045] Put 1000g 22-hydroxyl-20-methylpregn-4-en-3-one into a 5000ml three-necked flask, 2000ml toluene, add 300ml ethylene glycol, 200g...

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Abstract

The invention provides a method for synthesizing cholesterol and 25-hydroxycholesterol, which comprises the following steps of: 1) reacting 22-hydroxy-20-methylpregna-4-ene-3-ketone with pyrrolidine or ethylene glycol to protect 3-position carbonyl, then sulfonylating 22-position hydroxyl, and carrying out reduced pressure distillation to obtain 2-hydroxy-20-methylpregna-4-ene-3-ketone and 2-hydroxy-20-methylpregna-4-ene-3-ketone; cholesterol or 25-hydroxycholesterol is obtained through copper-catalyzed Grignard reagent substitution reaction and sodium borohydride reduction reaction. 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 and 25-hydroxycholesterol. 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 ...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 王涛李民强孟宪志万定建李佳霖罗觅纯
Owner 王涛
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