HCID 58109136, compound → HCID 58109725, compound

Participants

Reaction Steps

To a solution of (S)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(2-oxopropyl)-6-phenyl-1,3-oxazinan-2-one (150 mg, 0.39 mmol) in THF (10 mL) was added methylmagnesium bromide (1 M, 2.5 mL) under nitrogen at −78° C. The mixture was stirred at rt until the reaction was over. The reaction was quenched with satd aq NH4Cl. The organic phase was separated and concentrated to give crude product, which was purified by preparative HPLC to give (S)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (15 mg, 10%). 1H NMR (CDCl3): 1.05 (s, 3H), 1.10 (s, 3H), 1.45 (s, 3H), 2.10 (m, 1H), 2.16 (m, 2H), 2.20 (m, 1H), 2.33 (m, 1H), 2.76 (m, 1H), 5.60 (m, 1H), 6.16-6.58 (m, 1H), 6.78 (m, 2H), 6.86 (m, 2H), 7.26 (m, 5H).

Provenance & Evidence