sodium azide in tetrahydrofuran; acetone 12 h;

sodium azide in tetrahydrofuran; water T=0 - 20°C; 10.5 h; Cooling with ice;

1: 49 percent / DCC / dioxane / 24 h / 20 °C 2: 94 percent / aq. NaN3 / tetrahydrofuran; acetone / 12 h View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 85 °C 2: potassium hydroxide / ethanol; water / 3 h / Reflux 3: thionyl chloride / 2 h / 80 °C 4: sodium azide; N-benzyl-N,N,N-triethylammonium chloride / water; acetone; toluene / 10 - 15 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 85 °C 2: potassium hydroxide / ethanol; water / 3 h / Reflux 3: thionyl chloride / 2 h / 80 °C 4: sodium azide; N-benzyl-N,N,N-triethylammonium chloride / water; acetone; toluene / 10 - 15 °C View Scheme