Reaction Steps
To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-8-(allyloxy)-2-benzhydryl-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step F (15), 40 mg, 0.07 mmol) in EtOH (3 mL) was added a solution of LiOH (17 mg, 0.7 mmol) in H2O (0.6 mL). This reaction mixture was stirred at 110° C. for 5 h and stirred at 80° C. overnight. Ethyl ether (50 mL) was added to the mixture and washed with 1N HCl (40 mL) twice. The aqueous phase was basified to pH 12 with 50% aqueous NaOH solution. This mixture was extracted with ethyl acetate (120 mL). The organic layer was dried (Na2SO4), and concentrated in vacuo to give 40 mg of the title compound of Preparation F. 1H NMR (CDCl3, 500 MHz) δ 1.87 (3H, brd s), 2.38 (1H, dd, J=10, 15 Hz), 2.79 (1H, d, J=20 Hz), 2.96-2.99 (2H, m), 3.05 (1H, dd, J=5, 15 Hz), 3.62 (1H, m), 3.66 (1H, dd, J=5, 10 Hz), 3.71 (1H, d, J=20 Hz), 4.04 (1H, d, J=15 Hz), 4.33-4.40 (2H, m), 4.77 (1H, s), 5.08-5.15 (2H, m), 5.81 (1H, m), 6.63 (1H, d, J=10 Hz), 6.71-6.75 (1H, m), 6.79 (1H, d, J=10 Hz), 6.88 (2H, m), 7.10-7.21 (5H, m), 7.28-7.31 (2H, m), 7.40 (2H, d, J=10 Hz), 7.44 (2H, d, J=5 Hz). MS (ESI) (M+H)+ 541.22.
