hydrogen; palladium 10 on activated carbon in isopropyl alcohol T=42 - 45°C; P=3750.38 Torr; 5 h;

1.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 72 h / 20 °C / 760.05 Torr 2.1: dimethyl sulfoxide; phosphorus pentoxide / dichloromethane / 20 °C / Cooling with ice 2.2: 20 °C / Cooling with ice 3.1: sodium tris(acetoxy)borohydride; methanol / 2 h / 20 °C 4.1: hydrogenchloride / ethyl acetate; water / 1 h / 10 °C / pH 2 View Scheme

1.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 72 h / 20 °C / 760.05 Torr 2.1: dimethyl sulfoxide; phosphorus pentoxide / dichloromethane / 20 °C / Cooling with ice 2.2: 20 °C / Cooling with ice 3.1: sodium tris(acetoxy)borohydride; methanol / 2 h / 20 °C View Scheme

1.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 72 h / 20 °C / 760.05 Torr 2.1: dimethyl sulfoxide; phosphorus pentoxide / dichloromethane / 20 °C / Cooling with ice 2.2: 20 °C / Cooling with ice View Scheme

copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=40°C;

methanesulfonyl chloride; triethylamine; copper(l) iodide; triphenylphosphine; palladium dichloride in isobutyramide T=70 - 75°C; 8 h;

(i) EtMgBr, (ii) /BRN= 1209228/; Multistep reaction;