Hydrochloric Acid → HCID 58109700, compound

Participants

Reaction Steps

To a solution of (R)-6-allyl-3-((S)-1-benzylpiperidin-3-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (90 mg, 0.22 mmol) in THF (3 mL) was added BH3/THF (1 M, 0.44 mL) at 0° C. and the mixture was stirred at rt for 2 h. Then the mixture was cooled at 0° C., and H2O (0.2 ml), NaOH (3 M, 0.15 mL), 30% H2O2 (0.4 mL) were added. After the solution was stirred at rt for another 2 h, 1N aq HCl was added, and 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)-3-((S)-1-benzylpiperidin-3-yl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (30 mg, 30%). LC-MS Method 2 tR=0.976 min, m/z=427.7; 1H NMR (CDCl3): 1.28 (m, 2H), 1.36-1.45 (m, 1H), 1.58-1.67 (m, 6H), 1.88 (m, 2H), 2.10 (m, 1H), 2.17 (m, 1H), 2.48 (m, 1H), 2.64 (m, 2H), 3.12 (m, 1H), 3.34 (s, 2H), 3.48 (m, 2H), 4.05-4.15 (m, 1H), 6.94 (m, 2H), 7.15 (m, 5H), 7.22 (m, 2H).

Provenance & Evidence