4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=-4°C; 7 h;

1: H2 / Lindlar cat. / hexane 2: pyridine View Scheme

1: 1.) n-BuLi / 1.) THF/HMPA 2: H2 / Lindlar cat. / hexane 3: pyridine View Scheme

1: 1.) n-butyllithium, 2.) LiI / 1.) THF, from -78 deg C to 0 deg C, 2.) a.) DMEU, -78 deg C, b.) 20 deg C, 20 h 2: 72 percent / amberlyst 15 <H(1+) form> / methanol / 20 h / 40 °C 3: 96 percent / H2 4: 98 percent / DMAP, NEt3 / CH2Cl2 / 7 h / -4 °C View Scheme

1: 72 percent / amberlyst 15 <H(1+) form> / methanol / 20 h / 40 °C 2: 96 percent / H2 3: 98 percent / DMAP, NEt3 / CH2Cl2 / 7 h / -4 °C View Scheme