Production method of 25-hydroxycholesterol

A technology of hydroxycholesterol and its production method, which is applied in the direction of steroids and organic chemistry, can solve the problems of poor selectivity and low yield, and achieve the effects of short reaction time, reduced production cost and mild conditions

Active Publication Date: 2015-04-22
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main defect of this method is: selectivity is poor, and yield is relatively low

Method used

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  • Production method of 25-hydroxycholesterol
  • Production method of 25-hydroxycholesterol
  • Production method of 25-hydroxycholesterol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, a kind of production method of 25-hydroxycholesterol, carries out following steps successively:

[0037] 1) Add 20g of 24-dehydrocholesterol (about 0.052mol) and 0.2g of 4-dimethylaminopyridine (DMAP) to 150mL of pyridine (also used as a solvent and acid-binding agent), and add 10g (about 0.097mmol) acetic anhydride (dropped in about 30 minutes). The reaction process was monitored by TLC. After the dropwise addition, the reaction was continued at room temperature for 10 h, and the reaction ended.

[0038] The reaction solution was washed with water (the amount of water used was 50ml×2), pickled (using a dilute hydrochloric acid solution with a volume concentration of 5%, the amount used was 50ml×2), and then extracted with dichloromethane (the amount used was 30ml×3). Wash with saturated sodium bicarbonate solution until neutral, dry over anhydrous sodium sulfate (about 5 g) and remove the solvent (ie, dichloromethane) to obtain 19.1 g of acetylated 24-de...

Embodiment 2

[0047] Embodiment 2, a kind of production method of 25-hydroxycholesterol,

[0048] Utilize the hydroxybromination product of embodiment 1 step 2) gained, then carry out following step 3):

[0049] Dissolve 0.523 g of the hydroxy bromide product (1 mmol) in 20 mL of sodium ethoxide (0.27 g, 4 mmol) in ethanol, add 160 mg of Lindella catalyst (10% palladium content, 0.15 mmol of palladium), and the reaction mixture The reaction is carried out at 0°C and 0.1 MPa of hydrogen, and the reaction is stopped when the hydrogen pressure basically no longer drops (the reaction time is about 5 to 6 hours). The reaction results were detected by HPLC.

[0050] The resulting reaction solution was filtered, the filtrate was washed with 5% dilute hydrochloric acid solution and extracted with dichloromethane, the obtained extract was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution in turn, dried with anhydrous sodium sulfate, and rotated under reduced p...

Embodiment 3

[0051] Embodiment 3, a kind of production method of 25-hydroxycholesterol,

[0052] Utilize the hydroxybromination product of embodiment 1 step 2) gained, then carry out following step 3):

[0053] 0.523 g of hydroxybrominated product (1 mmol) was dissolved in 40 mL of glycerol solution, 210 mg of Lindella catalyst (5% palladium content, 0.1 mmol), 0.08 g of sodium hydroxide solid (2 mmol) were added, and the reaction mixture was The reaction is carried out in 0.1MPa hydrogen at 20°C, and the reaction is stopped when the hydrogen pressure basically no longer drops (the reaction time is about 5 to 6 hours). The reaction results were detected by HPLC.

[0054] The resulting reaction solution was filtered, the filtrate was washed with 5% dilute hydrochloric acid solution and extracted with dichloromethane, the obtained extract was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution in turn, dried with anhydrous sodium sulfate, and rotated und...

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Abstract

The invention discloses a production method of 25-hydroxycholesterol. The production method comprises the following steps: 1) protecting 3-hydroxyl of 24-dehydrocholesterol to obtain acylated 24-dehydrocholesterol; 2) reacting the acylated 24-dehydrocholesterol with deionized water and a halogenating reagent in a solvent at a temperature ranging from -20 DEG C to -1 DEG C for 2-4 hours to obtain a hydroxyhalogenated product; and 3) reacting the hydroxyhalogenated product with hydrogen in an organic solvent under the catalysis of an alkali and a Lindlar catalyst to obtain the 25-hydroxycholesterol. The production method of the 25-hydroxycholesterol, which is disclosed by the invention, is relatively mild in conditions, relatively short in reaction time and reliable in results because the Lindlar catalyst is used for reaction; as the hydrogen is used as a hydrogen source, the production cost of the production method is reduced and the production method is green and clean.

Description

technical field [0001] The present invention relates to a method for producing 1,25-(OH) 2 D. 3 The production method of 25-hydroxycholesterol, an important intermediate, especially relates to a method for preparing 25-hydroxycholesterol by catalytic hydrogenation. Background technique [0002] Vitamin D 3 Belonging to steroid derivatives, it plays an important role in the formation of bones. It can promote the absorption of calcium and phosphorus in the intestinal tract, ensure the content of these two elements in body fluids, and promote the normal calcification of bones. Vitamin D deficiency in the body 3 , Rickets may occur in children, and osteomalacia may occur in adults. Vitamin D 3 The anti-rickets effect is mainly through 1,25-(OH) 2 D. 3 to achieve, its biological activity strength is vitamin D 3 10000 times. 25-hydroxycholesterol as 1,25-(OH) 2 D. 3 The important precursor of , its synthesis is particularly important. [0003] The structural formula o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 陈新志赵倩计立钱国平刘建刚王子强
Owner ZHEJIANG UNIV
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