10-(benzyl(methyl)amino)-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide → N-(4-Fluorobenzyl)-3-hydroxy-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide

To a solution of 10-(benzyl(methyl)amino)-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (255 mg, 0.432 mmol) in methanol (2 mL) was added Pd/C (32.2 mg, 0.030 mmol) and the mixture was stirred under hydrogen atmosphere (balloon) for 1 h. The catalyst was then filtered off, and the filtrate was evaporated under reduced pressure to afford the title compound as a white solid (200 mg, 93% yield). 1H NMR (300 MHz, DMSO-d6) δ: 12.3 (1 H, s), 9.5 (1 H, s), 7.3-7.4 (2 H, m), 7.2-7.2 (2 H, m), 4.5 (2 H, d, J=6.22 Hz), 4.0 (2 H, d, J=3.29 Hz), 2.6 (3 H, brs), 2.0-2.1 (4 H, m), 1.7-1.9 (5 H, m). LCMS (M+H)=387.17.