water; triphenylphosphine in tetrahydrofuran T=20°C;

1: With di-isopropyl azodicarboxylate; triphenylphosphine in tetrahydrofuran 0.0833333 h; 2: With diphenylphosphoranyl azide in tetrahydrofuran T=100°C; 24 h;

sodium azide in N,N-dimethyl-formamide T=20°C;

sodium azide in dimethyl sulfoxide

sodium azide in methanol; water T=70°C; 24 h; Yield given;

1: With N,N-dimethyl acetamide; (Ph3P)3RhCl; benzo[1,3,2]dioxaborole in dichloromethane T=0°C; 5 h; RefluxInert atmosphere; 2: With benzenesulphonyl azide; t-BuON=NOt-Bu in N,N-dimethyl-formamide T=80°C; Inert atmosphere; regioselective reaction;

1: 930 mg / sodium borohydride / methanol / 0.17 h / Ambient temperature 2: 850 mg / pyridine / 4 h / 0 °C 3: sodium azide / methanol; H2O / 24 h / 70 °C View Scheme

1: 925 mg / aq. hydrochloric acid / tetrahydrofuran / 1 h / Ambient temperature 2: 930 mg / sodium borohydride / methanol / 0.17 h / Ambient temperature 3: 850 mg / pyridine / 4 h / 0 °C 4: sodium azide / methanol; H2O / 24 h / 70 °C View Scheme

1: 1.18 g / ceric ammonium nitrate / acetonitrile / 0.05 h / Ambient temperature 2: 925 mg / aq. hydrochloric acid / tetrahydrofuran / 1 h / Ambient temperature 3: 930 mg / sodium borohydride / methanol / 0.17 h / Ambient temperature 4: 850 mg / pyridine / 4 h / 0 °C 5: sodium azide / methanol; H2O / 24 h / 70 °C View Scheme

1: 9.1 g / n-butyl-lithium / tetrahydrofuran; hexane / 1.) -78 --> -23 deg C, 1.5 h, 2.) 0 deg C, 14 h 2: 1.18 g / ceric ammonium nitrate / acetonitrile / 0.05 h / Ambient temperature 3: 925 mg / aq. hydrochloric acid / tetrahydrofuran / 1 h / Ambient temperature 4: 930 mg / sodium borohydride / methanol / 0.17 h / Ambient temperature 5: 850 mg / pyridine / 4 h / 0 °C 6: sodium azide / methanol; H2O / 24 h / 70 °C View Scheme