Reaction Steps
To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-benzhydryl-8-hydroxy-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step F (14), 40 mg, 0.076 mmol) in DMF (2 mL) were added potassium carbonate (52 mg, 0.38 mmol) and allyl bromide (73 mg, 0.61 mmol). The mixture was stirred at rt overnight. Ethyl acetate (100 mL) was added and the mixture was washed with H2O (70 mL) twice, and dried over Na2SO4, and concentrated under vacuum to give the title compound: 1H NMR (CDCl3, 500 MHz) δ 2.50 (1H, m), 2.76 (1H, d, J=15 Hz), 2.90 (1H, d, J=35 Hz), 3.19 (1H, m), 3.26 (1H, dd, J=5, 10 Hz), 3.75 (1H, d, J=20 Hz), 3.80 (1H, m), 4.00 (1H, m), 4.13 (1H, d, J=20 Hz), 4.40 (2H, m), 4.72 (1H, dd, J=5, 10 Hz), 4.83 (1H, s), 4.87 (1H, s), 5.12-5.17 (2H, m), 5.84 (1H, m), 6.65 (1H, d, J=10 Hz), 6.75-6.80 (4H, m), 7.13-7.16 (1H, m), 7.19-7.32 (6H, m), 7.36 (2H, d, J=5 Hz), 7.42 (2H, d, J=5 Hz). MS (ESI) (M+H)+ 567.19.
