hydrogen bromide in water T=120°C; 16 h;

1: hydrogenchloride; iron / ethanol; water / 2 h / Reflux 2: potassium hydroxide / ethanol / 15 h / Reflux 3: hydrogen bromide / water / 16 h / 120 °C View Scheme

1: potassium hydroxide / ethanol / 15 h / Reflux 2: hydrogen bromide / water / 16 h / 120 °C View Scheme

1: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 2: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 3: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme

1.1: hydrogenchloride / water / 8 h / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / |Inert atmosphere 2.2: 20 h / 0 - 25 °C / |Inert atmosphere 3.1: lithium borohydride / tetrahydrofuran / 21 h / 25 °C / |Inert atmosphere 4.1: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere 5.1: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 6.1: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 7.1: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / |Inert atmosphere 1.2: 20 h / 0 - 25 °C / |Inert atmosphere 2.1: lithium borohydride / tetrahydrofuran / 21 h / 25 °C / |Inert atmosphere 3.1: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere 4.1: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 5.1: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 6.1: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme

1: lithium borohydride / tetrahydrofuran / 21 h / 25 °C / |Inert atmosphere 2: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere 3: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 4: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 5: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme

1: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere 2: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 3: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 4: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme