Ethyl Acetate → HCID 67272289, compound

Participants

Reaction Steps

To a solution of (4S,5R)-4-(3,5-difluorobenzyl)-5-((R)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step A(7), 320 mg, 0.93 mmol) in THF (20 mL) was added 4-methoxybenzaldehyde (253 mg, 1.86 mmol) and acetic acid (2 drops). This mixture was stirred at rt overnight. NaBH(OAc)3 (588 mg, 2.78 mmol) was added and the reaction mixture was stirred at rt for 2 days. Ethyl acetate (300 mL) was added and the mixture was washed with aqueous sodium carbonate, H2O, dried (Na2SO4), and concentrated in vacuo. Crude mixture was purified by silica gel Flash Chromatography to give 420 mg of the title compound (80% yield): 1H NMR (CDCl3, 500 MHz) δ 2.57 (1H, t, J=10 Hz), 2.96 (1H, dd, J=5, 20 Hz), 3.17 (1H, dd, J=5, 15 Hz), 3.44-3.50 (2H, m), 3.68 (2H, dd, J=10, 45 Hz), 3.80 (3H, s), 3.84-3.88 (3H, m), 4.66 (1H, dd, J=5, 10 Hz), 5.29 (1H, s), 6.71-6.74 (3H, m), 6.88 (2H, d, J=10 Hz), 6.98 (1H, d, J=5 Hz), 7.15-7.21 (5H, m). MS (ESI) (M+H)+ 465.12.

Provenance & Evidence