反应详情

温度

-78 °C

In a nitrogen atmosphere, 5.26 mL of diethylaminosulfur trifluoride was added to chloroform (160 mL) solution of 5.51 g of benzyl 4-(2-chlorophenyl)-4-hydroxypiperidine-1-carboxylate at −78° C., and stirred for 1 hour at −78° C. Water was added to the reaction liquid, and extracted with chloroform. The chloroform layer was dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was dissolved in 150 mL of acetone/water (2:1) mixture. 15.9 mL of aqueous 0.05 M osmium tetroxide solution and 3.73 g of N-methylmorpholine N-oxide were added thereto, and stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 2.11 g of the entitled compound as a colorless oily substance.

1. extractionextracted with chloroform
2. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
3. customThe solvent was evaporated off under reduced pressure
4. dissolutionthe residue was dissolved in 150 mL of acetone/water (2:1) mixture
5. addition15.9 mL of aqueous 0.05 M osmium tetroxide solution and 3.73 g of N-methylmorpholine N-oxide were added
6. stirringstirred overnight at room temperature
7. customThe reaction liquid
8. washwashed with aqueous sodium hydrogencarbonate solution
9. dry with materialdried with anhydrous sodium sulfate
10. customThe solvent was evaporated off under reduced pressure
11. customthe residue was separated
12. custompurified through silica gel column chromatography (hexane/ethyl acetate=10/1)