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Method for preparing 7-dehydrocholesterol

A technology for dehydrocholesterol and cholesterol, applied in the direction of steroids, organic chemistry, etc., can solve the problems of many by-products, harmful environment, and restricting development, and achieve the effects of less side reactions, less corrosive equipment, and simple operation

Active Publication Date: 2013-07-24
ANHUI BBCA FERMENTATION TECH ENG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Traditional Vitamin D 3 The synthesis of the precursor adopts the method of adding a bromine to the 7-position of cholesterol and then eliminating a molecule of hydrogen bromide, but this method has many by-products and is harmful to the environment, which restricts the development of this method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1) Add 5g of cholesterol to 40ml of acetyl chloride, reflux at 100°C for 8h, and react to form cholesterol acetate. The purity of the cholesterol acetate produced by the reaction determined by the internal standard method was 94%, and the yield was 90%.

[0033] 2) Dissolve 5g of cholesterol acetate in 70ml of cyclohexanone, shake well at room temperature, and heat to 50°C. Take 0.3g of selenium dioxide and add it to the reaction solution in batches, and add it in 30 minutes. React at 80°C for 8h, cool down to room temperature, and then cool with 3°C water to precipitate crystals, filter with suction, and dry in vacuum at 50°C for 6h. The purity of the 7-carbonylcholesterol acetate obtained through detection is 86%, and the yield is 65%.

[0034] 3) Dissolve 5 g of 7-carbonylcholesterol acetate and 8 g of p-toluenesulfonyl hydrazide in 50 ml of absolute ethanol, stir at room temperature and monitor with thin layer chromatography, stop the reaction after 15 hours, and ...

Embodiment 2

[0037] 1) Add 5g of cholesterol to 40ml of benzoyl chloride, reflux at 80°C for 6h, and react to generate cholesterol benzoate. The purity of the cholesterol benzoate generated by the reaction determined by the internal standard method was 96%, and the yield was 93%.

[0038] 2) Dissolve 5g of cholesterol benzoate in 70ml of cyclohexanone, shake well at room temperature, and heat to 50°C. Take 0.5g of potassium permanganate and add to the reaction liquid in batches, and the addition is completed within 30 minutes. React at 50°C for 5h, cool down to room temperature, and then cool with 3°C water to precipitate crystals, filter with suction, and dry in vacuum at 50°C for 6h. The purity of 7-carbonylcholesterol benzoate obtained through detection is 87%, and the yield is 69%.

[0039] The following steps are the same as steps 3, 4, and 5) in Example 1.

Embodiment 3

[0041] In this embodiment, step 2) is different from embodiment 1, and other steps are the same as embodiment 1 step. Step 2) of the present embodiment is:

[0042] 2) Dissolve 5g of cholesterol acetate in 70ml of cyclohexanone, shake well at room temperature, and heat to 50°C. Take 0.2 g of dicobalt trioxide and add it to the reaction solution in batches, and the addition is completed in 30 minutes, and oxygen is continuously introduced. React at 90°C for 6h, cool down to room temperature, and then cool with 3°C water to precipitate crystals, filter with suction, and dry in vacuum at 50°C for 6h. The purity of the 7-carbonylcholesterol acetate obtained through detection is 91%, and the yield is 75%.

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Abstract

The invention relates to a method for preparing 7-dehydrocholesterol, which comprises the following steps: 1) protecting hydroxyl on the 3-site of cholesterol; 2) oxidizing carbon on the 7-site of the product obtained in step 1) into carbonyl; 3) carrying out a hydrazone reaction on the product obtained in step 2) and a hydrazine derivative; 4) reacting the product obtained in step 3) with a strongly alkaline reagent; and 5) reacting the product obtained in step 4) with water or an acid. The method has the advantages of simple operation process, less secondary reaction, high yield and less corrosion to equipment, thereby having high industrial production values.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for preparing vitamin D 3 The method of precursor 7-dehydrocholesterol. Background technique [0002] Vitamin D 3 It is an essential fat-soluble vitamin for the growth, reproduction, maintenance of life and health of humans, livestock and livestock. Its main function is to regulate calcium and phosphorus metabolism, promote intestinal calcium and phosphorus absorption and bone calcification, and maintain blood calcium. and blood phosphorus balance. Vitamin D 3 It is mainly used in the three aspects of pharmaceutical preparations, food additives and feed additives. As a pharmaceutical preparation, it is mainly used clinically to treat diseases such as Kuru's disease, ricket disease, osteoporosis, and hypothyroidism; as a food and beverage additive , it can be added to milk, dairy products, biscuits, candies and various beverages to prevent vitamin D deficiency; vitamin D...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 李荣杰尚海涛吴鹏举何玉春张望
Owner ANHUI BBCA FERMENTATION TECH ENG RES
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