1: 76 percent / LiN3, p-toluenesulfonic acid / hexamethylphosphoric acid triamide / 3 h / 100 °C 2: 78 percent / acetic acid / 0.5 h / 100 °C 3: 1.) H2 / 1.) 10 percent Pd/C / 1.) EtOH-H2O, 2h, 40 psi 4: 59 percent / H2O View Scheme

lithium azide; toluene-4-sulfonic acid in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=100°C; 3 h;

lithium azide in N,N-dimethyl-formamide T=150°C; 3 h;

1: 76 percent / LiN3, p-toluenesulfonic acid / hexamethylphosphoric acid triamide / 3 h / 100 °C 2: 78 percent / acetic acid / 0.5 h / 100 °C View Scheme