1.1: hydrogen / 5 palladium on charcoal / methanol / 16 h / 20 °C / 3375.34 Torr / Inert atmosphere 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / Inert atmosphere; Reflux 2.2: 0.5 h / 20 °C / Cooling with ice View Scheme

1.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 2.1: hydrogen / 5 palladium on charcoal / methanol / 16 h / 20 °C / 3375.34 Torr / Inert atmosphere 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / Inert atmosphere; Reflux 3.2: 0.5 h / 20 °C / Cooling with ice View Scheme

1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C 1.2: 5 °C 2.1: hydrogenchloride / water / 5 h / 55 °C 2.2: 20 °C / pH 12 3.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 20 °C / Inert atmosphere View Scheme

1.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 6 h / 25 - 30 °C 2.1: sodium hydroxide / dimethyl sulfoxide / 0.17 h / 20 - 25 °C 2.2: 2 h / 50 - 55 °C View Scheme

1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 4 h / 50 - 55 °C 2.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 6 h / 25 - 30 °C 3.1: sodium hydroxide / dimethyl sulfoxide / 0.17 h / 20 - 25 °C 3.2: 2 h / 50 - 55 °C View Scheme

1.1: acetone; methanol 2.1: diethylamine / tert-butyl methyl ether 3.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C 3.2: 5 °C 4.1: hydrogenchloride / water / 5 h / 55 °C 4.2: 20 °C / pH 12 5.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 20 °C / Inert atmosphere View Scheme

1.1: trifluoroacetic acid 2.1: acetone; methanol 3.1: diethylamine / tert-butyl methyl ether 4.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C 4.2: 5 °C 5.1: hydrogenchloride / water / 5 h / 55 °C 5.2: 20 °C / pH 12 6.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 20 °C / Inert atmosphere View Scheme

1.1: diethylamine / tert-butyl methyl ether 2.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C 2.2: 5 °C 3.1: hydrogenchloride / water / 5 h / 55 °C 3.2: 20 °C / pH 12 4.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 20 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 1.2: 2.5 h / -78 - 0 °C 2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -40 °C / |Inert atmosphere 2.2: 0.17 h / -40 °C 2.3: 2 h / -40 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 3.2: 1.5 h / -78 - -50 °C 4.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 4 h / 20 °C / |Cooling with ice 5.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 20 °C / |Cooling with ice 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / |Cooling with ice View Scheme

1: With hydrogen; palladium on activated carbon in water T=45°C; P=750.075 - 3750.38 Torr; 2: With sodium hydroxide in water Product distribution / selectivity;