Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.C([O-])([O-])=O.[Na+].[Na+].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>CCO>[C:19]1([CH2:18][NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
To a solution of 3-aminoquinuclidine dihydrochloride (8.0 g, 40.0 mmol) in EtOH (100 mL) was added excess Na2CO3 and the mixture was stirred for 1 h and then filtered. To this solution was added benzaidehyde (3.2 g, 30.0 mmol) and the reaction was stirred at room temperature for 2 h and then NaBH4 (3 pellets, 0.4 g ea.) was added and the reaction was stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue was partitioned between 10% Na2CO3 and EtOAc. The organic layer was separated, dried over K2CO3, filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (92/8 CHCl3/1.0 M NH3 in MeOH) to give N-phenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (4.2 g, 76%) as an intermediate, a pale yellow oil. MH+=217. 1H NMR (CDCl3) 1.4 (m, 3H), 1.7 (m, 1H), 1.9 (m, 2H), 2.45 (2m, 1H), 2.8 (m, 5H), 3.2 (m, 1H), 3.75 (d, 2H), 7.3 (m, 5H).
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