Ethanol → 9-Methyl-9-azabicyclo(3.3.1)nonan-3-amine

To a 250 mL RB flask were added 9-methyl-9-azabicyclo[3.3.1]nonan-3-one (10 g), NH2OH.HCl (5.26 g), NaOAc.3H2O (10.26 g), EtOH (56 mL), and H2O (26 mL). The mixture was refluxed for 1.5 h and cooled to RT. Solvents were removed and the residue was partitioned between aqueous K2CO3 (3M) and CHCl3. The organic phase was separated and the aqueous phase extracted twice with CHCl3. The combined CHCl3 solution was washed once with brine, dried over Na2SO4, filtered, and evaporated to a brownish oil, which solidified upon standing. The solid was transferred to a 500 mL Parr flask. To this were added Raney-Ni (6.2 g, wet) and NH3 solution in MeOH (150 mL), made by bubbling NH3 into MeOH for 20 min. This mixture was hydrogenated under a pressure of 40-45 psi of H2 at RT for 18 h. The mixture was filtered through a pad of Celite. All volatiles were removed on a rotary evaporator. EtOH (50 mL) was added to the residue and then evaporated to give an I-1 as an oil (9.5 g, 94%). This crude product contained two isomers, and was used without further purification.