Multi-step reaction with 9 steps
1: 1.) CuCN / 1.) PhMe, Et2O, 0 deg C, 2 min, 2.) PhMe, Et2O, from -78 deg C to -20 deg C, 45 min
2: 64 percent / Et3N, Pd(OAc)2, tri-o-tolylphosphine / acetonitrile / 20 h / 125 °C
3: 99 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 2 h / 0 °C
4: 100 percent / CH2Cl2 / 16 h / Ambient temperature
5: 62 percent / H2 / 10percent Pd/C / ethanol / 21 h / 2327.2 Torr / Ambient temperature
6: Et3N / CH2Cl2 / 0.5 h / 0 °C
7: CH2Cl2; dimethylsulfoxide / 18.5 h / Ambient temperature
8: 100 percent / H2, NH3 / Raney Ni / methanol; NH3; H2O / 4 h / 2585.7 Torr / Ambient temperature
9: 41 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / Ambient temperature
With
dmap; palladium diacetate; ammonia; hydrogen; diisobutylaluminium hydride; triethylamine; tris-(o-tolyl)phosphine;
palladium on activated charcoal; nickel;
In
methanol; ethanol; dichloromethane; ammonia; water; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1021/jm00101a014