hydrogenchloride in tetrahydrofuran; ethanol; water T=20°C; 6 h; Inert atmosphere;

1.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / |Inert atmosphere 2.1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 20 °C / |Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / methanol / 2 h / 20 °C / |Inert atmosphere 4.1: NaIO3 / acetone; water / 0.17 h / 20 °C / |Inert atmosphere 4.2: 20 h / 20 °C / |Inert atmosphere 5.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 6.1: hydrogenchloride / ethanol; water; tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1.1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 20 °C / |Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / methanol / 2 h / 20 °C / |Inert atmosphere 3.1: NaIO3 / acetone; water / 0.17 h / 20 °C / |Inert atmosphere 3.2: 20 h / 20 °C / |Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 5.1: hydrogenchloride / ethanol; water; tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1.1: palladium 10 on activated carbon; hydrogen / methanol / 2 h / 20 °C / |Inert atmosphere 2.1: NaIO3 / acetone; water / 0.17 h / 20 °C / |Inert atmosphere 2.2: 20 h / 20 °C / |Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 4.1: hydrogenchloride / ethanol; water; tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1.1: NaIO3 / acetone; water / 0.17 h / 20 °C / |Inert atmosphere 1.2: 20 h / 20 °C / |Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 3.1: hydrogenchloride / ethanol; water; tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 2: hydrogenchloride / ethanol; water; tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme