hydrogen; MCM-silylamine Pd(II) in methanol T=20°C; Reduction; 2 h;

1: 95 percent / HN3; DEAD; PPh3 2: LiAlH4 / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 67 percent / NaBH4; BF3*Et2O 2: 95 percent / HN3; DEAD; PPh3 3: LiAlH4 / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 67 percent / xylene / Heating 2: 67 percent / NaBH4, I2 / tetrahydrofuran / 6 h / Heating 3: 72 percent / triphenylphosphine, diethyl azodicarboxylate, azidoic acid / benzene / 3 h / Ambient temperature 4: 90 percent / H2 / 10percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature View Scheme

in dichloromethane Ambient temperature;