1: With tetra(n-butyl)ammonium hydrogensulfate in acetonitrile 3 h; Heating; 2: With ammonia in methanol T=60°C; 4 h;

potassium carbonate in N,N-dimethyl-formamide T=110°C; Inert atmosphere;

1.1: diphenylphosphoryl azide; Et3N / dimethylformamide / 6 h / 20 °C 2.1: 4.695 g / dimethylformamide; methanol / 8 h / 65 °C 3.1: 59 percent / KOH / ethane-1,2-diol / 1.5 h / 110 - 115 °C 4.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 4.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme

1.1: 4.695 g / dimethylformamide; methanol / 8 h / 65 °C 2.1: 59 percent / KOH / ethane-1,2-diol / 1.5 h / 110 - 115 °C 3.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 3.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme

1.1: 75 percent / H2 / 10 percent Pd/C / methanol / 1.5 h / 20 °C / 2068.59 Torr 2.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 2.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme

1.1: 1.37 g / p-TsOH*H2O / CH2Cl2 / 24 h / 20 °C 2.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 2.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme

1.1: benzene / 2 h / Heating 1.2: NaBH4 / ethanol / 24 h / 20 °C 2.1: 1.37 g / p-TsOH*H2O / CH2Cl2 / 24 h / 20 °C 3.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 3.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme

1.1: 59 percent / KOH / ethane-1,2-diol / 1.5 h / 110 - 115 °C 2.1: tetrabutylammonium hydrogen sulfate / acetonitrile / 3 h / Heating 2.2: 56 percent / NH3 / methanol / 4 h / 60 °C View Scheme