反应详情

温度

0 °C

To a solution of ditrichloromethyl carbonate (2.38 g, 8.02 mmol, 1.50 equiv) in dichloromethane (20 mL) was added a solution of 3-[(tert-butyldimethylsilyl)oxy]azetidine (1 g, 5.34 mmol, 1.00 equiv) in dichloromethane (5 mL) dropwise with stirring at 0° C. over 30 min. Stirring was continued for 30 min whereupon a solution of triethylamine (810 mg, 8.00 mmol, 1.50 equiv) in dichloromethane (5 mL) was added dropwise with stirring at 0° C. in 30 min. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 20 mL of sodium bicarbonate (sat.). The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined, washed with 2×40 mL of sodium chloride (sat.), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15). Purification afforded 1.3 g (97%) of 3-[(tert-butyldimethylsilyl)oxy]azetidine-1-carbonyl chloride as a light yellow liquid.

1. stirringStirring
2. additionwas added dropwise
3. stirringwith stirring at 0° C. in 30 min
4. stirringThe resulting solution was stirred overnight at room temperature
5. customThe reaction was then quenched by the addition of 20 mL of sodium bicarbonate (sat.)
6. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
7. washwashed with 2×40 mL of sodium chloride (sat.)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customPurification