1: 1,2-dichloro-ethane / 0.67 h / 0 °C / |Reflux 2: methanol / 2 h / |Reflux 3: hydrogen bromide / water / 2 h / |Reflux 4: sodium hydroxide / tert-butyl alcohol / 2 h / 45 - 50 °C 5: C56H72IrNOP(1+)*C32H12BF24(1-); caesium carbonate; hydrogen / methanol / 12 h / 60 °C / 4560.31 Torr / |Autoclave View Scheme

1: sodium hydroxide / tert-butyl alcohol / 2 h / 45 - 50 °C 2: C56H72IrNOP(1+)*C32H12BF24(1-); caesium carbonate; hydrogen / methanol / 12 h / 60 °C / 4560.31 Torr / |Autoclave View Scheme

1.1: tetrahydrofuran / 18 h / 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 2.2: 0.67 h / -78 °C 3.1: ethanol / 18 h / 45 °C 4.1: N-bromosuccinmide / dichloromethane; acetonitrile 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C 5.2: 4 h / 20 °C View Scheme

hydrogenchloride in dichloromethane T=30°C; 2 h; Solvent;

1: With borane-THF in tetrahydrofuran T=20°C; 16 h; 2: With sodium hydroxide; water in tetrahydrofuran T=0°C; 48 h; Heating / reflux;

1: With borane-THF in tetrahydrofuran T=20°C; 16 h; 2: With sodium hydroxide; water in tetrahydrofuran T=0°C; 48 h; Heating / reflux;

hydrogenchloride in dichloromethane T=30°C; 2 h; Solvent;

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: acetic acid / 2 h / 65 °C / Inert atmosphere View Scheme

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere 3.2: -15 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 4.2: 0 - 20 °C 5.1: sodium tetrahydroborate / methanol / 20 °C 6.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C 7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 8.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C 9.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 10.1: dichloromethane / 1 h / 20 °C 11.1: triethylamine / dichloromethane 12.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: (3R)-Piperidine-1,3-dicarboxylic acid 1-tert-butyl ester With 1,1'-carbonyldiimidazole in tetrahydrofuran T=0°C; 1 h; 2: O,N-dimethyl-hydroxylamine hydrochloride With triethylamine in tetrahydrofuran T=0 - 20°C;