pyridine; hydrogen; Lindlar's catalyst in methanol

1: APTS / CH2Cl2 / Ambient temperature 2: 80 percent / 1.) BuLi; 2.) HMPA / tetrahydrofuran; hexane / 1.) 0-5 deg C; 2.) r.t., 30 min 3: 100 percent / pyridine, H2 / 5percent Pd/CaCO3 with 3.5percent lead / methanol View Scheme

1: 80 percent / 1.) BuLi; 2.) HMPA / tetrahydrofuran; hexane / 1.) 0-5 deg C; 2.) r.t., 30 min 2: 100 percent / pyridine, H2 / 5percent Pd/CaCO3 with 3.5percent lead / methanol View Scheme

carbon tetrabromide; triphenylphosphine in dichloromethane Ambient temperature;