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25-hydroxy-7-dehydrocholesterol synthetic method

A technique for the synthesis of dehydrocholesterol, which is applied in the fields of steroids and organic chemistry, can solve problems such as cumbersome steps, and achieve the effects of high reaction efficiency, good reaction selectivity, and high yield

Active Publication Date: 2015-09-16
ZHEJIANG UNIV OF TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, after follow-up research, it was found that there is still a lot of room for improvement. This method uses low temperature (-20°C) and strong alkali conditions, and the raw material is sulfonyl hydrazone, which is unstable in air and water. The reaction preparation of analogous compounds and sulfonyl hydrazide requires separation and purification, and the steps are still relatively cumbersome

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0022] At room temperature, 4.86 g (10 mmol) of 25-hydroxycholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 1.19g (22 mmol) sodium methoxide were successively added into the ball milling tank, and the ball milling reaction was carried out for 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet Crystalline, 25-hydroxy-7-dehydrocholesterol 3.52g, yield 88%, melting point 191~193℃, 1 H NMR (400 MHz, CDCl 3 ) δ = 5.55 - 5.57 (m, 1H), 5.36 - 5.39 (m, 1H), 3.59-3.67 (m, 1H), 2.44 - 2.49 (m, 1H), 2.25 - 2.31(m, 1H), 2.06 - 2.11(m, 1H), 1.87 - 1.99(m, 4H), 1.54 - 1.75 (m, 7H), 1.26 - 1.51 (m, 11H), 1.22 (s, 6H), 1.02 - 1.10 ...

Embodiment 2

[0024] At room temperature, 4.86 g (10 mmol) of 25-hydroxycholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 0.18g (22 mmol) lithium hydride were successively added into the ball milling tank, and the ball milling reaction was carried out for 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet 25-hydroxy-7-dehydrocholesterol 3.48g, yield 87%, melting point 191~193℃.

Embodiment 3

[0026] At room temperature, 4.86 g (10 mmol) of 25-hydroxycholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 0.86g (22 mmol) sodium amide were successively added to the ball milling tank, and the ball milling reaction was 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet 25-hydroxy-7-dehydrocholesterol 3.56g, yield 89%, melting point 191~193℃.

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Abstract

The present invention relates to a 25-hydroxy-7-dehydrocholesterol synthetic method, a 25-hydroxy-7-keto-cholesterol derivative is used as a raw material for mechanical milling reaction in a ball mill pot under the effect of sulfonyl hydrazide and a base in the absence of an organic solvent, and then hydrolysis reaction is performed to obtain 25-hydroxy-7-dehydrocholesterol synthetic method. According to the method, in the absence of a solvent, mechanical milling reaction is performed, no dust is spilled over in the grinding process, reaction controllability is good, reaction efficiency is high, the solvent recovery operation in the post-processing process can be avoided, operation is simplified, environmental pollution is reduced, the reaction selectivity is good, yield is high, operation is simple, cost is low, post-treatment is simple, three-waste is less, product is easy to separate, purity is high, the yield is up to 89%, the melting process is short, and the product purity is high.

Description

technical field [0001] The invention relates to a method for synthesizing 25-hydroxyl-7-dehydrocholesterol. Background technique [0002] 25-hydroxy-7-dehydrocholesterol aka 25-hydroxyvitamin D 3 Originally, 25-hydroxyvitamin D can be synthesized by ultraviolet light irradiation 3 , 25-Hydroxyvitamin D 3 Also known as calcifediol, vitamin D 3 The active metabolites of the liver in the body have stronger physiological activities and can be used as feed additives, which have been widely used in animal breeding. [0003] 25-Hydroxyvitamin D 3 The market is very good, and it has been widely used in the breeding industry in Europe, so the market potential of the key intermediate 25-hydroxy-7-dehydrocholesterol is very large. Before the present invention, 25-hydroxy-7-dehydrocholesterol was generally prepared from 25-hydroxycholesterol derivatives through bromination-debromination reaction. The reaction formula is as follows (Journal of Organic Chemistry, 2005, 70(21), 8513-...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 金灿苏为科王子强刘建刚钱国平方礼貌
Owner ZHEJIANG UNIV OF TECH
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