1: 98 percent / sodium azide; 1,4-diaza-bicyclo[2.2.2]octane; 4-dimethylaminopyridine / benzo-15-crown-5 / CH2Cl2 / 20 h / 40 °C 2: 99 percent / hydrogen / Pd/C / methanol / 2 h 3: aq. HCl / 20 h / Heating 4: NaOH; NaHCO3 / H2O / 63 h 5: 74 mg / hydrogen / Pd/C / methanol / 2 h View Scheme

1: 98 percent / sodium azide; 1,4-diaza-bicyclo[2.2.2]octane; 4-dimethylaminopyridine / benzo-15-crown-5 / CH2Cl2 / 20 h / 40 °C 2: 99 percent / hydrogen / Pd/C / methanol / 2 h 3: aq. HCl / 20 h / Heating 4: NaOH; NaHCO3 / H2O / 63 h View Scheme