1: LiAlH4 2: (tosylation) View Scheme

(tosylation);

1: 930 mg / sodium borohydride / methanol / 0.17 h / Ambient temperature 2: 850 mg / pyridine / 4 h / 0 °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 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 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 View Scheme

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

in diethyl ether