HCID 58109706, compound → HCID 25182140, compound

Participants

Reaction Steps

To a solution of methyl 3-bromophenyl(3-oxo-3-phenylpropyl)carbamate (250 mg, 0.69 mmol) in dry THF (2 mL) was added dropwise 1 M allylmagnesium bromide (10 mL) −78° C. The reaction mixture was stirred at rt for 3 h. The resulting mixture was quenched with sattd aq NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to give 6-allyl-3-(3-bromophenyl)-6-phenyl-1,3-oxazinan-2-one (120 mg, 47%). 1H NMR (400 MHz, CDCl3): δ=2.48 (m, 2H), 2.55-2.7 (m, 2H), 3.23 (m, 1H), 3.51 (m, 1H), 5.04 (m, 2H), 5.72 (m, 1H), 7.01 (m, 1H), 7.11 (m, 1H), 7.23 (m, 1H), 7.3 (m, 1H), 7.35 (m, 6H).

Provenance & Evidence