Acetone → HCID 25182554, compound

Participants

Reaction Steps

To a solution of 6-allyl-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (7.1 mg, 0.018 mmol) in acetone (0.5 mL) was added NMO.H2O (6 mg, 0.044 mmol), then OsO4 (10 μL, 2.5 wt % in 2-Me-2-propanol). The reaction was stirred overnight at rt. The solvent was evaporated and the residue was redissolved in EtOAc. The organic layer was washed with 10% aq Na2S2O3 (2×), 1M aq HCl (2×) and brine (1×). The organic layer was dried over Na2SO4, filtered, evaporated, and purified by prep HPLC to afford 3-(2′,4′-difluorobiphenyl-3-yl)-6-(2,3-dihydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (6.53 mg). LC-MS Method 1, m/z=440 (M+H)+. 1H NMR (CDCl3) 7.47-7.33 (m), 7.15-7.12 (m), 6.96-6.86 (m), 3.51 (br m), 3.37-3.26 (m), 2.69 (br m), 2.58-2.48 (m), 2.29-2.23 (m), 2.14 (d), 2.06 (d).

Provenance & Evidence