1403864-73-2

1403864-74-3

To a solution of benzyl 4-hydroxybicyclo[2.2.2]octan-1-yl carbamate (14.8 g, 53 mmol) in methanol (200 mL) was added palladium carbon catalyst (0.5 g, 10% w/w). The reaction mixture was placed at 50 °C and the reaction was stirred overnight in a hydrogen atmosphere (50 Psi). Upon completion of the reaction, the catalyst was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was dissolved in a methanol solution of hydrochloric acid (10% v/v, 50 mL) and stirred at room temperature for 2 hours. Subsequently, the reaction mixture was concentrated again under reduced pressure, tetrahydrofuran (THF, 20 mL) was added and stirred for 1 h at room temperature. The precipitated solid was collected by filtration and dried to give 4-aminodicyclo[2.2.2]octan-1-ol hydrochloride (6.7 g, 36 mmol, 70% yield). The product was characterized by 1H NMR (DMSO-d6): δ 8.00 (s, 3H), 4.48 (br s, 1H), 1.76-1.80 (m, 6H), 1.58-1.61 (m, 6H). The mass spectrum (ESI) showed m/z 142.1 [M+H]+.