1: 85 percent / aq. acetic acid / 4 h / 55 °C 2: 67 percent / Ph3P, pyridine, aq. NH3 View Scheme

1: 70 percent / 80percent acetic acid / 0.33 h / Heating 2: pyridine / 24 h / 4 °C 3: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 4: 31 percent / NH3 / methanol / 144 h / Ambient temperature 5: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

lithium azide in N,N-dimethyl-formamide T=85°C; 2 h;

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=100°C; 5 h;

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

1: 88 percent / 1N NaOH / ethanol; H2O / 4 h / Heating 2: 91 percent / pyridine / 24 h / Ambient temperature 3: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C View Scheme

1: 93 percent / pyridine / 24 h / 4 °C 2: 88 percent / 1N NaOH / ethanol; H2O / 4 h / Heating 3: 91 percent / pyridine / 24 h / Ambient temperature 4: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C View Scheme

1: 91 percent / pyridine / 24 h / Ambient temperature 2: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C View Scheme

1.1: pyridine; 4-(N,N-dimethlyamino)pyridine / Inert atmosphere; Heating 2.1: pyridine / 0 - 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 30 h / 20 °C / Inert atmosphere 4.1: N,N,N',N,-tetramethylethylenediamine; trimethylsilylazide; LiF / N,N-dimethyl-formamide / 1 h / 105 °C / Inert atmosphere 4.2: 20 h / 110 °C / Inert atmosphere View Scheme