Sodium hydride → HCID 58485274, compound

Participants

Reaction Steps

To a solution of methyl tert-butyl(3-hydroxy-3-phenylhex-5-enyl)carbamate (600 mg, 1.97 mmol) in dry THF (10 mL) was added NaH (236 mg, 5.91 mmol) at 0° C. under N2, and the mixture was stirred at rt overnight. The reaction was quenched with water, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford the crude product, which was purified by preparative TLC to give 6-allyl-3-tert-butyl-6-phenyl-1,3-oxazinan-2-one (325 mg, 61%). 1H NMR (CDCl3): 1.23 (s, 9H), 2.01-2.21 (m, 1H), 2.28-2.34 (m, 1H), 2.45-2.59 (m, 2H), 2.71-2.81 (m, 1H), 3.13-3.21 (m, 1H), 4.92-5.02 (m, 2H), 5.53-5.63 (m, 1H), 7.21-7.34 (m, 5H).

Provenance & Evidence