1: With triphenylphosphine in tetrahydrofuran T=20°C; 0.166667 h; 2: With water in tetrahydrofuran T=20°C; 28 h;

hydrogen; Ni(Raney)

2: hydrogen / Ni(Raney) View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; oil / 0.17 h / 0 - 20 °C 1.2: 4 h / 95 °C 2.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 90 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.2: 28 h / 20 °C View Scheme

1.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 90 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 2.2: 28 h / 20 °C View Scheme

hydrogen; Pd/Al2O3 in water T=110°C; P=75007.5 Torr; 7 h;

1: formaldehyde hydrazone; orthoformic acid triethyl ester in methanol 3 h; Heating; 2: 3-(dodecyloxy)-1-propylamine in methanol 10 h; Heating;