A suspension of LAH (38.0 mg, 1.00 mmol) in ether (1 mL) was stirred under nitrogen and cooled to 0° C. A solution of (3R,4aR,12bS)-3-(benzyloxy)-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazole-12b-carbonitrile (33, R1=4-Fluorophenyl, R3=Trifluoromethyl, Rx=Benzyl) (89 mg, 0.167 mmol) in THF (3 mL) was added maintaining reaction temperature under 5° C. and the mixture was allowed to stir at rt for about 54 h. The reaction was diluted with THF (2 mL) and quenched by addition of water (40 μL), then 2N NaOH (40 μL) and then water (80 μL). The reaction was stirred overnight at rt. The mixture was dried with Na2SO4 and filtered through Celite®, rinsing with THF (5 mL) and EtOAc (10 mL). The combined organics were concentrated under reduced pressure to yield crude ((3R,4aR,12bS)-3-(benzyloxy)-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-12b-yl)methanamine (34, R1=4-Fluorophenyl, R3=Trifluoromethyl, Rx=Benzyl). LC/MS, method 3, Rt=2.41 min, MS m/z 538 (M+H)+. The residue was used in step #3 without further purification.
