hydrogen; palladium 10 on activated carbon in methanol; water T=25°C; P=3750.38 Torr; 2 h;

methanol; sodium tetrahydroborate; NiII chloride hexahydrate T=40 - 45°C; 12 h; Reagent/catalystTemperatureTime;

trifluoroacetic acid 2 h; Heating;

1: With trifluoroacetic acid in dichloromethane T=0°C; 0.75 h; 2: With 4-methyl-morpholine

1.1: sodium hydroxide 2.1: diethylamine / ethyl acetate / Reflux 2.2: Reflux 3.1: sulfuric acid / 12 h / Reflux 4.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 5.1: triethylamine / dichloromethane / 3 h / 0 °C 6.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 7.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 7.2: 20 h / 20 °C 8.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 9.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 10.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 11.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 2: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 2.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 2.2: 20 h / 20 °C 3.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 5.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 6.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 7.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 1.2: 20 h / 20 °C 2.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 4.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 6.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 2: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 3: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 4: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 3: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme