1: 1.) H2 / 1.) 10percent Pd/C / 1.) CH3OH, CH2Cl2, 24 h, 2.) toluene, reflux, 12 h 2: 66 percent / CH2Cl2 / 72 h 3: 60 percent / BuLi / hexane; tetrahydrofuran / 10 h / -70 °C 4: 1.) hydrochloric acid, 2.) ammonia / 1.) H2O, room temperature, 16 h, 2.) H2O View Scheme

1: 1.) H2 / 1.) 10percent Pd/C / 1.) CH3OH, CH2Cl2, 24 h, 2.) toluene, reflux, 12 h 2: 66 percent / CH2Cl2 / 72 h View Scheme

hydrogen; palladium on activated charcoal 1.) CH3OH, CH2Cl2, 24 h, 2.) toluene, reflux, 12 h; Yield given. Multistep reaction;

1: 1.) H2 / 1.) 10percent Pd/C / 1.) CH3OH, CH2Cl2, 24 h, 2.) toluene, reflux, 12 h 2: 66 percent / CH2Cl2 / 72 h 3: 60 percent / BuLi / hexane; tetrahydrofuran / 10 h / -70 °C 4: 1.) hydrochloric acid, 2.) ammonia / 1.) H2O, room temperature, 16 h, 2.) H2O View Scheme