1.1: zinc / ethanol / 1 h / 70 °C 2.1: sodium carbonate / ethanol / 1 h / 50 °C 3.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 6.2: 3 h / 20 °C 7.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 8.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C 9.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 10.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 12.1: hydrogenchloride; water / methanol / 1 h View Scheme

1.1: zinc / ethanol / 1 h / 70 °C 2.1: sodium carbonate / ethanol / 1 h / 50 °C 3.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 6.2: 3 h / 20 °C 7.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 8.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C View Scheme

hydrogen; triethylamine; 1 Pd/C in methanol T=20°C; 24 h; Inert atmosphere;

1: zinc / ethanol / 1 h / 70 °C 2: sodium carbonate / ethanol / 1 h / 50 °C 3: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 5: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

1: zinc / ethanol / 1 h / 70 °C 2: sodium carbonate / ethanol / 1 h / 50 °C 3: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C View Scheme