1: triphenyphosphine, hydrazoic acid, diethyl azodicarboxylate / benzene / 1 h / Ambient temperature 2: triphenylphosphine, water / tetrahydrofuran / 15 h / 60 °C 3: DMAP / CH2Cl2 / 1 h / Ambient temperature 4: 78 percent / H2, 10percent HCl / 10percent Pd/C / ethanol / 1 h / 60 °C View Scheme

1: triphenyphosphine, hydrazoic acid, diethyl azodicarboxylate / benzene / 1 h / Ambient temperature 2: triphenylphosphine, water / tetrahydrofuran / 15 h / 60 °C 3: Et3N / dioxane; H2O / 20 h / Ambient temperature 4: 70 percent / H2, 10percent HCl / 10percent Pd/C / ethanol / 1 h / 60 °C View Scheme