反应详情

温度

0 °C

Sodium hydride (60% dispersion in mineral oil, 12 g, 0.3 mol) was added slowly to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4-hydroxy-4-(2-propenyl)-1-piperidinecarboxylate (Description 129, 23.1 g, 0.096 mol) in dimethylformamide (200 mL) and the mixture was stirred at 0° C. for 10 minutes. Allyl bromide (25.4 ml, 0.3 mol) was added and the mixture was stirred at 0° C. for 5 minutes, then at room temperature for 45 minutes. The mixture was cooled to 0° C. and water (200 mL) was added. The mixture was extracted with diethyl ether (2×200 mL) and the combined organic fractions were washed with water (4×200 mL) and brine (150 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (9:1), to give the title compound (5.5 g, 20%). m/z (E) 226 (M+1-C4H8).

1. stirringthe mixture was stirred at 0° C. for 5 minutes
2. waitat room temperature for 45 minutes
3. temperatureThe mixture was cooled to 0° C.
4. extractionThe mixture was extracted with diethyl ether (2×200 mL)
5. washthe combined organic fractions were washed with water (4×200 mL) and brine (150 mL)
6. dry with materialdried (MgSO4)
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by flash column chromatography on silica gel
9. washeluting with isohexane/EtOAc (9:1)