Sodium hydride → HCID 58109194, compound

Participants

Reaction Steps

To a suspension of NaH (55 g, 1.4 mmol) in THF (10 mL) at 0° C. was added a solution of methyl (S)-1-(4-bromophenyl)ethyl(3-(2-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate (300 mg, 0.68 mmol) in THF (10 mL). The resulting mixture was stirred for 10 minutes, and then was refluxed for 1 h. The reaction was quenched with saturated aq NH4Cl solution, and the solution was extract with EtOAc. The combine organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC to afford (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 35%) and (S)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 35%).

Provenance & Evidence