Sodium hydride → 3-(1-(4-Bromophenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

Participants

Reaction Steps

To a solution of methyl 1-(4-bromophenyl)cyclopropyl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (58.8 mg, 0.129 mmol) in dry THF (10 mL) was added NaH (60% in mineral oil, 10 mg, 2 equiv). The mixture was heated to reflux for 2 h. LC-MS found the reaction was complete. The mixture was cooled to rt, quenched with satd aq NH4Cl (3 mL), diluted with EtOAc (30 mL), washed with 1% aq HCl (5 mL), satd aq NaHCO3 solution (5 mL) and brine (4 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 12-g silica gel column, eluted with a 0˜20% EtOAc in hexanes gradient, to afford 3-(1-(4-bromophenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (33.4 mg, 61%).

Provenance & Evidence