hydrogen; palladium in water; acetic acid; tert-butyl alcohol Yield given;

1: NaHCO3 / CH2Cl2 / 0.25 h 2: 4-(aminomethyl)piperidine silica reagent / CH2Cl2 / 0.25 h 3: NaHCO3 / CH2Cl2 / 0.25 h 4: 4-(aminomethyl)piperidine silica reagent / CH2Cl2 / 0.25 h 5: NaHCO3 / CH2Cl2 / 0.33 h 6: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 24 h / 2327.17 Torr / Ambient temperature View Scheme