Borane;tetrahydrofuran → HCID 25182553, compound

Participants

Reaction Steps

To a 0° C. solution of 6-allyl-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (18 mg, 0.045 mmol) in THF (1 mL) was added BH3.THF (60 μL, 1M THF solution) and the mixture was stirred overnight at rt. The reaction was cooled to 0° C. and NaBO3.H2O (19 mg, 0.20 mmol) was added and stirred for 2 h warming to rt. The solvent was removed in vacuo and the residue was redissolved in CH3CN (4 mL). The solution was filtered and purified by prep HPLC to afford 3-(2′,4′-difluorobiphenyl-3-yl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (4.44 mg). LC-MS Method 1, tR=1.97 min, m/z=424 (M+H). 1H NMR (CDCl3) 7.47-7.33 (m), 7.32-7.26 (m), 7.16-7.12 (m), 6.96-6.85 (m), 4.28 (t), 3.52-3.13 (m), 3.36-3.27 (m), 2.5-2.47 (m), 2.15-1.99 (m).

Provenance & Evidence