76272-56-5

6164-67-6

76272-41-8

9-Methyl-9-azabicyclo[3,3,1]nonan-3-one oxime (10 g, 0.06 mol) was used as a raw material and dissolved in methanol (70 mL) and 0.88 ammonia. The hydrogenation reaction was carried out at 50 °C and 50 psi (344.8 kPa) hydrogen pressure for 16 h using 5% rhodium/carbon catalyst (1 g dry weight). Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by filtration. The catalyst bed was washed with methanol and the methanol solution was subsequently evaporated under reduced pressure to afford endo-3-amino-9-methyl-9-azabicyclo[3,3,1]nonane as an oil (8.6 g, 93% yield), which solidified to a waxy solid (8.6 g, 93%) upon standing. EI analysis by GC/MS (JEOL DX303) showed the molecular ion peak m/z 154 (M+).