Hydrochloric Acid → HCID 58109148, compound

Participants

Reaction Steps

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(3-fluorophenyl)ethyl)-1,3-oxazinan-2-one (80 mg, 0.392 mmol) in dry THF (4 mL) was added dropwise BH3.THF (0.2 mL, 0.2 mmol, 1 M) at 0° C. After stirring for 2 h at rt, the reaction mixture was cooled to 0° C. and water (1 mL), aqueous NaOH (0.5 mL, 3 M) and H2O2 (0.3 mL, 30%) were added successively. The mixture was stirred for 2-3 h at rt and diluted with water (8 mL). The pH was adjusted to 6-7 with 0.5 N aq HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×6 mL). The combined organic layers were washed with a satd aq NaHCO3 (10 mL) and brine (10 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford (R)-6-(4-fluorophenyl)-3-((S)-1-(3-fluorophenyl)ethyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (40 mg, 48%). LC-MS Method 2 tR=2.151 min, m/z=332.1; 1H NMR (CDCl3): 1.31 (m, 1H) 1.49 (m, 3H), 1.64 (m, 1H), 1.81-1.93 (m, 2H), 2.14-2.26 (m, 3H), 2.88 (m, 1H), 3.51 (m, 2H), 5.68 (m, 1H), 6.96 (m, 2H), 7.13 (m, 1H), 7.19 (m, 4H), 7.37 (m, 1H).

Provenance & Evidence