Reaction Steps
rac-(2′R,4aS,12bS)-9-(4-fluorophenyl)-12b-(pyridin-2-ylmethyl)-2,4,4a,5,6,7,9,12b-octahydro-1H-spiro[benzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridine-3,2′-oxirane] (119, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (1.865 g, 4.10 mmol) was suspended in EtOH (41.0 mL). NaBH4 (0.776 g, 20.52 mmol) was added to the then the mixture was warmed to about 65° C. for about 2 h. The mixture was cooled then concentrated under reduced pressure. Water (50 mL) was added to the material then the solids were collected by filtration and dried the material was purified on silica gel (120 g) using a gradient from 0-10% MeOH in DCM. Product fractions were combined and concentrated under reduced pressure to yield rac-(3R,4aS,12bS)-9-(4-fluorophenyl)-3-methyl-12b-(pyridin-2-ylmethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-3-ol (120, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl, R3=Methyl) (1.87 g, 99%); LC/MS, method 2, Rt=2.65 min, MS m/z 457 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.42-8.35 (m, 2H), 8.28-8.26 (m, 1H), 8.18 (s, 1H), 7.62 (s, 1H), 7.46-7.37 (m, 3H), 7.05-7.02 (m, 1H), 6.58 (d, J=7.8 Hz, 1H), 4.10 (s, 1H), 3.70 (d, J=12.6 Hz, 1H), 3.56-3.49 (m, 1H), 3.44-3.32 (m, 1H), 2.91 (d, J=12.8 Hz, 1H), 2.66-2.53 (m, 2H), 2.15-1.80 (m, 3H), 1.70-1.59 (m, 2H), 1.53-1.30 (m, 2H), 1.16-1.14 (m, 2H), 0.92 (s, 3H).
