Borane;tetrahydrofuran → HCID 66857639, compound

Participants

Reaction Steps

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (500 mg, 1.6 mmol) in THF (20 mL) was added BH3/THF (1 M, 3.2 mL) at 0° C. The mixture was stirred at rt for 2 h. The mixture was quenched with H2O (2.5 mL) at 0° C., then NaOH (3 M, 1.1 mL) and 30% H2O2 (2.5 mL) were added. After stirring at rt for another 2 h, 1N HCl was added to the mixture. The mixture was extracted with EtOAc. The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (320 mg, 62%).

Provenance & Evidence