1.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 3.2: 3 h / 20 °C 4.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 5.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C 6.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 7.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 9.1: hydrogenchloride; water / methanol / 1 h View Scheme

1.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 3.2: 3 h / 20 °C 4.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 5.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

palladium 10 on activated carbon; hydrogen in methanol T=30°C; P=2250.23 Torr; 18 h;