hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 10 h; Ambient temperature;

sodium tetrahydroborate in isopropyl alcohol T=70°C; 6 h;

1: 1-benzyl-2-oxo-piperidine With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride in dichloromethane T=-78 - 0°C; 1 h; Inert atmosphere; 2: halo(propyl)magnesium in diethyl ether; dichloromethane T=-78 - 20°C; 1 h; Inert atmosphere; 3: With lithium aluminium tetrahydride in diethyl ether; dichloromethane T=20°C; 1 h; Inert atmosphere;

1: 1-benzyl-2-oxo-piperidine With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride in dichloromethane T=-78°C; 0.75 h; 2: n-propyl-magnesium bromide in diethyl ether; dichloromethane T=-78 - 20°C; 1 h; 3: With lithium aluminium tetrahydride in diethyl ether; dichloromethane T=20°C; 1 h;

in tetrahydrofuran Ambient temperature;

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 2 h 2: 64 percent / NaBH4 / propan-2-ol / 6 h / 70 °C View Scheme

1.1: lithium triethylborohydride / tetrahydrofuran / 1 h / -70 - 0 °C / |Schlenk technique; |Inert atmosphere 1.2: 0 °C / pH 9.5 / |Schlenk technique; |Inert atmosphere 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -80 - 0 °C / |Schlenk technique; |Inert atmosphere 2.2: 2 h / -80 - -10 °C / |Schlenk technique; |Inert atmosphere 3.1: sodium tetrahydroborate / ethanol / 48 h / 0 °C 4.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 72 h / 20 °C / 3750.38 Torr View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -80 - 0 °C / |Schlenk technique; |Inert atmosphere 1.2: 2 h / -80 - -10 °C / |Schlenk technique; |Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 48 h / 0 °C 3.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 72 h / 20 °C / 3750.38 Torr View Scheme

1.1: acetone / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 2.1: KPF6 / water / 24 h / 20 °C 3.1: lithium triethylborohydride / tetrahydrofuran / 1 h / -70 - 0 °C / |Schlenk technique; |Inert atmosphere 3.2: 0 °C / pH 9.5 / |Schlenk technique; |Inert atmosphere 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -80 - 0 °C / |Schlenk technique; |Inert atmosphere 4.2: 2 h / -80 - -10 °C / |Schlenk technique; |Inert atmosphere 5.1: sodium tetrahydroborate / ethanol / 48 h / 0 °C 6.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 72 h / 20 °C / 3750.38 Torr View Scheme

1.1: acetone / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 2.1: KPF6 / water / 24 h / 20 °C 3.1: lithium triethylborohydride / tetrahydrofuran / 1 h / -70 - 0 °C / |Schlenk technique; |Inert atmosphere 3.2: 0 °C / pH 9.5 / |Schlenk technique; |Inert atmosphere 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -80 - 0 °C / |Schlenk technique; |Inert atmosphere 4.2: 2 h / -80 - -10 °C / |Schlenk technique; |Inert atmosphere 5.1: sodium tetrahydroborate / ethanol / 48 h / 0 °C 6.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 72 h / 20 °C / 3750.38 Torr View Scheme