Synthesis method of cholesterol
A cholesterol and compound technology, applied in the field of organic chemical synthesis, can solve the problems of expensive catalysts, high prices, and low product purity, and achieve the effects of avoiding pathogenic bacteria and virus infection, facilitating industrial production, and simple synthesis steps
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Embodiment 1
[0101] Example 1 Preparation of compound of formula (2)
[0102]
[0103] The present embodiment provides the preparation results of the compound of formula (2) under different experimental conditions:
[0104] (1) Dichloromethane (50 mL), BA (4.96 g, 15 mmol), TEMPO (23.6 mg, 0.15 mmol), sodium bicarbonate (1.76 g, 21 mmol), NCS (2.3 g, 17.3 mmol) were sequentially added to the flask , tetrabutylammonium bromide (0.484 g, 1.5 mmol) and water (32 mL), react at 0 °C for 6 h. After the reaction was detected by TLC, sodium thiosulfate pentahydrate solution (1.12g sodium thiosulfate pentahydrate / 22mL water) was added, stirred at 5-10°C for 20min, separated, and the aqueous phase was extracted with dichloromethane (50mL×2), The organic layers were combined, washed with 1% sodium hydroxide solution (20 mL), and the layers were separated. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the compound of formula (2) (white ...
Embodiment 2
[0107] Example 2 Preparation of compound of formula (3)
[0108]
[0109] The present embodiment provides the preparation results of the compound of formula (3) under different experimental conditions:
[0110] (1) Toluene (50 mL), triphenylphosphine (4.79 g, 18.28 mmol) and 3,3-dimethylallyl bromide (2.72 g, 18.28 mmol) were added to the flask, the temperature was heated and refluxed for 2 h, and then cooled. To 0°C, potassium tert-butoxide (2.05g, 18.28mmol) was added, and after stirring for 0.5h, the compound of formula (2) (4.618g, 14.06mmol) was added in batches, and the mixture was reacted at 10°C for 0.5h. After monitoring the reaction by TLC, water (5 mL) was added to quench the reaction, 2M HCl was added to adjust the pH to 6-7, the organic phase was washed with water (50 mL×2), and concentrated under reduced pressure to obtain a milky white solid. The above solid was added to 50% ethanol (16 mL), slurried at 25°C for 1 h, filtered, and the filter cake was rinsed ...
Embodiment 3
[0115] Example 3 Preparation of compound of formula (4)
[0116]
[0117] The present embodiment provides the preparation results of the compound of formula (4) under different experimental conditions:
[0118] (1)N 2 Under protection, add tert-butanol (30 mL) and potassium tert-butoxide (4.48 g, 40 mmol) to the flask, stir at 35 ° C for 30 min, add the compound of formula (3) (3.8 g, 10 mmol) to the above mixture, 35 ° C Stir for 2h. After the completion of the reaction monitored by TLC, the reaction solution was cooled to 25°C, poured into a stop solution made of ice water (100mL)\glacial acetic acid (5g)\sodium ascorbate (2.5g), the solid was precipitated, continued stirring for 20min, filtered, The filter cake was purified by beating with ethanol / water to obtain compounds of formula (4) (4E and 4Z, 3.12 g of white solids, 82.1% molar yield).
[0119] (2)N 2 Under the protection, tert-butanol (30 mL) and potassium tert-butoxide (3.36 g, 30 mmol) were added to the fla...
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