1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol 4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h 6: Dowex W-50 (H+ form) / methanol / 16 h 7: H2, 1,2-diaminoethane, P2-Ni / ethanol 8: pyridine View Scheme

1: 1. lithium amide / 1. THF, liquid ammonia, 1 h; 2. 3 h 2: 93 percent / Na / liquid ammonia; diethyl ether / 7 h 3: Dowex W-50(H(1+)) / methanol / 6 h View Scheme

1: 1. lithium amide / 1. THF, liquid ammonia, 1 h; 2. 3 h 2: 93 percent / Na / liquid ammonia; diethyl ether / 7 h 3: Dowex W-50(H(1+)) / methanol / 6 h 4: 94 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol 4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h 6: Dowex W-50 (H+ form) / methanol / 16 h View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol 4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol 4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h 6: Dowex W-50 (H+ form) / methanol / 16 h 7: 66 percent / sodium, 1,2-ethanediol / toluene / 2 h / 98 - 100 °C 8: pyridine View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h View Scheme

Multi-step reaction with 2 steps 1: 1. lithium amide / 1. THF, liquid ammonia, 1 h; 2. 3 h2: 93 percent / Na / liquid ammonia; diethyl ether / 7 h