tert-butylamine hydrobromide in tetrahydrofuran 0 deg C, 1 h, r.t., overnight;

in ammonia T=-40°C; 2 h;

n-butyllithium 1.) THF, hexane, from -78 deg C to RT, 2.) THF, hexane, reflux, 21 h; Yield given. Multistep reaction;

1: 95 percent / dimethylsulfoxide / 5 h / 100 - 110 °C 2: 2.) conc. HCl / 1.) ether, reflux, 7h, 2.) water, reflux, 2h 3: 5.8 g / hydrogene / Lindlar catalyst / hexane / 20 °C View Scheme

1: 95 percent / dimethylsulfoxide / 5 h / 100 - 110 °C 2: 8 g / hydrogene / Lindlar catalyst / hexane / 20 °C View Scheme

1: 86 percent / NaI / acetone / 15 h / Heating 2: 1.) n-BuLi / 1.) THF, hexane, from -20 deg C to RT, 20 min, 2.) THF, hexane, from -78 deg C to RT 3: 1.) n-BuLi / 1.) THF, hexane, 2.) THF, hexane, from -78 deg C to RT 4: CuCl2/SiO2 / CH2Cl2 / 48 h / Ambient temperature View Scheme