1: 5 g / palladium acetate, tri-o-tolylphosphine, N,N-diisopropylethylamine / acetonitrile / 90 °C 2: 5 g / H2 / 10percent Pd/C / ethanol; tetrahydrofuran / 2585.7 Torr 3: hydrazine hydrate / ethanol / 1.5 h / 80 °C View Scheme

1: n-BuLi / diethyl ether; hexane / Ambient temperature 2: 5 g / palladium acetate, tri-o-tolylphosphine, N,N-diisopropylethylamine / acetonitrile / 90 °C 3: 5 g / H2 / 10percent Pd/C / ethanol; tetrahydrofuran / 2585.7 Torr 4: hydrazine hydrate / ethanol / 1.5 h / 80 °C View Scheme