Allyl bromide → Tert-butyl 4-(allyloxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a suspension of NaH (0.48 g, 11.9 mmol; 60% dispersion) in dry DMF (50 mL) at 0° C. was added a solution of 21-2 (2.0 g, 9.9 mmol) in DMF (15 mL). After 10 min, the cooling bath was removed, but then returned after another 10 min, followed by addition of allyl bromide (4.3 mL, 50 mmol). After 1.5 h, the reaction was quenched with 10% KHSO4 and then diluted with H2O (90 mL). The reaction mixture was extracted with EtOAc, the layers separated, and the EtOAc portion washed with H2O, 5% KHSO4, sat. NaHCO3 and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 20% EtOAc/hexanes) gave 21-3 as a yellowish oil. Rf 0.47 (silica, 20% EtOAc/hexanes).

Provenance & Evidence