1: H2 / Lindlar catalyst / hexane / 25 °C 2: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 3: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 4: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 5: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 6: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

With  quinoline; hydrogen in  methanol T=20°C; 0.5 h;  stereoselective reaction;  Show Experimental Procedure  

Multi-step reaction with 3 steps 1: 69 percent / NaBH4, H2, Ni(OAc)2 * 4 H2O / ethanol2: 81 percent / potassium fluoride dihydrate / dimethylformamide / 5 h3: 78 percent / n-butylamine, cuprous iodide / tetrakis (triphenylphosphine) palladium / benzene / 6 h / Ambient temperature  

Multi-step reaction with 3 steps 1: H2 / Lindlar catalyst / hexane / 25 °C2: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C3: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C