lithium aluminium tetrahydride in diethyl ether 3 h; Heating;

1: tetrahydrofuran / 12 h / Ambient temperature 2: pyridine / dichloromethane / 2 h / 0 °C 3: trifluoroacetic acid / 48 h / 50 °C 4: sodium azide / N,N-dimethyl-formamide / 80 °C 5: sodium periodate / acetonitrile / 1 h / 0 °C 6: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme

1: pyridine / dichloromethane / 2 h / 0 °C 2: trifluoroacetic acid / 48 h / 50 °C 3: sodium azide / N,N-dimethyl-formamide / 80 °C 4: sodium periodate / acetonitrile / 1 h / 0 °C 5: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme

1: trifluoroacetic acid / 48 h / 50 °C 2: sodium azide / N,N-dimethyl-formamide / 80 °C 3: sodium periodate / acetonitrile / 1 h / 0 °C 4: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal

1: sodium periodate / acetonitrile / 1 h / 0 °C 2: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme

1: trifluoroacetic acid 2: sodium periodate / acetonitrile / 1 h / 0 °C 3: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme

1: sodium azide / N,N-dimethyl-formamide / 80 °C 2: sodium periodate / acetonitrile / 1 h / 0 °C 3: lithium aluminium tetrahydride / diethyl ether / 3 h / Heating View Scheme