Reaction Steps
rac-(4aR,13bS)-9-(4-Fluorophenyl)-13 b-(pyridin-2-ylmethyl)-1,2,4,4a,5,6,7,13 b-octahydrospiro[benzo[3,4]cyclohepta[1,2-d][1,2,3]triazolo[1,5-a]pyridine-3,2′-[1,3]dioxolane] (156, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.230 g, 0.475 mmol) in acetone (3 mL) was treated with 6 N hydrochloric acid (0.060 mL, 0.322 mmol) then stirred at rt for about 3 h. Sat. aq. NaHCO3 (˜5 mL) and EtOAc (15 mL) were added to the mixture then the layers were separated. The organic layer was washed with brine (˜5 mL) then dried over MgSO4, filtered and concentrated in vacuo to yield rac (4aR,13bS)-9-(4-fluorophenyl)-13b-(pyridin-2-ylmethyl)-4,4a,5,6,7,13b-hexahydro-1H-benzo[3,4]cyclohepta[1,2-d][1,2,3]triazolo[1,5-a]pyridin-3(2H)-one (157, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.142 g, 68%); LC/MS, method 3, Rt=2.30 min, MS m/z 441 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.40 (s, 1H), 8.36-8.27 (m, 1H), 8.12 (s, 1H), 8.11-8.03 (m, 2H), 7.48-7.30 (m, 3H), 7.08-6.98 (m, 1H), 6.64 (d, J=7.8 Hz, 1H), 3.85-3.73 (m, 1H), 3.55-3.42 (m, 2H), 2.75-2.64 (m, 1H), 2.42-2.23 (m, 3H), 2.20-2.02 (m, 5H), 1.79-1.68 (m, 1H), 1.49-1.36 (m, 1H), 1.29-1.21 (m, 1H).
