反应详情

温度

23 °C

To a stirring solution of (2R,3R)-2-styryl-tetrahydro-pyran-3-carboxylic acid (106 mg, 0.456 mmol) in anhydrous tert-butanol (5 mL) under nitrogen in a flame-dried round bottom flask was added sequentially triethylamine (95 μL, 0.684 mmol) and diphenylphosphoryl azide (98 μL, 0.456 mmol). The reaction was warmed to reflux conditions and maintained at reflux for 15 h. The reaction solution was then cooled to 23° C., concentrated, and purified by flash chromatography (SiO2, 30% ethyl acetate in hexanes) to yield the desired carbamate (76.4 mg, 55.5%) as a white solid. MS (ESI), m+/z: (M+H)+=304.3.

1. temperatureThe reaction was warmed
2. temperatureto reflux conditions
3. temperaturemaintained
4. temperatureat reflux for 15 h
5. concentrationconcentrated
6. custompurified by flash chromatography (SiO2, 30% ethyl acetate in hexanes)