hydrogen; 5 Pd(II)/C(eggshell) in methanol T=25°C; P=735.572 Torr; 10 h;

1: With potassium carbonate; Pd-Tedicyp catalyst in N,N-dimethyl-formamide T=110°C; Heck reaction; 20 h; 2: With sodium hydroxide; water in N,N-dimethyl-formamide T=50 - 80°C;

1: With sodium hydroxide; isopropyl alcohol T=20°C; 6 h; 2: With hydrogenchloride; water

hydrogenchloride; water 4.5 h; Product distribution / selectivity;

1.1: piperidine / pyridine / 50 - 75 °C / Inert atmosphere 1.2: 0 °C / Cooling with ice 2.1: hydrogen / palladium 10 on activated carbon / methanol / 2.5 h / 750.08 Torr View Scheme

1.1: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 15 h / 110 °C / Inert atmosphere 1.2: 15 h / 20 °C / 760.05 Torr 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 48 h / 20 °C View Scheme

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 15 h; Inert atmosphere;

1: (R)-lt;1-(1-Naphthyl)ethylgt;ammonium chloride With sodium hydroxide in toluene 2: 3-[3-(trifluoromethyl)phenyl]propanoic acid in toluene T=140 - 150°C; Further stages.;

1: With borane-THF in tetrahydrofuran T=0 - 20°C; 25 h; 2: With water in tetrahydrofuran; methanol

1.1: dimethylsulfide borane complex / toluene / 40 - 85 °C 2.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 15 h / 25 - 40 °C 3.1: potassium carbonate / N-benzyl-N,N,N-triethylammonium chloride / isobutyl methylketone / 1 h / 20 °C 3.2: 15 h / 85 - 90 °C 4.1: potassium carbonate; thiophenol; N-benzyl-N,N,N-triethylammonium chloride / dimethyl sulfoxide / 24 h / 25 - 35 °C 4.2: 2 h / 0 - 25 °C View Scheme