Water → HCID 58109301, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-6-allyl-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (0.2780 g, 0.686 mmol, 1.0 equiv) in THF (20 mL) was degassed and then cooled with an ice-salt bath (−9° C.). To this solution was added a solution of 1.0 M BH3.THF complex in THF (1.5 mL, 1.5 mmol, 2.2 equiv). The resulting mixture was allowed to slowly warm to rt while stirring overnight (21 h) and then quenched with H2O (3 mL) and NaBO3.H2O (0.680 g, 6.8 mmol, 10 equiv). The mixture was vigorously stirred at rt overnight and then diluted with CH2Cl2, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to give 0.2337 g (80%) of (R)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one. LC-MS Method 1 tR=1.59 min, m/z 446 (MNa+), 380, 210, 171; 1H NMR (400 MHz, CD3OD) δ 7.27-7.23 (m, 2H), 7.04 (t, J=8.8 Hz, 2H), 6.94 (d, J=8.5 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.67 (t, J=74.1 Hz, 1H), 5.48 (q, J=7.1 Hz, 1H), 3.43-3.39 (m, 2H), 3.07-3.02 (m, 1H), 2.42-2.37 (m, 1H), 2.26-2.10 (m, 2H), 1.91-1.85 (m, 2H), 1.58-1.50 (m, 1H), 1.46 (d, J=7.0 Hz, 3H), 1.29-1.20 (m, 1H); 19F NMR (376 MHz, CD3OD) δ −83.95 (d, J=73.8 Hz), −117.51 (m).

Provenance & Evidence