sodium azide in dimethyl sulfoxide T=20°C; 18 h;

1: With phosphorus tribromide in diethyl ether T=20°C; 2: With sodium azide in N,N-dimethyl-formamide T=80°C;

1: sulfuric acid; sodium tetrahydroborate / chloroform; methanol 2: phosphorus tribromide / dichloromethane 3: sodium azide / N,N-dimethyl-formamide / 80 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 20 °C / |Inert atmosphere 2: phosphorus tribromide / diethyl ether / 16 h 3: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme