hydrogen; ammonium formate; palladium on activated charcoal in ethanol 6 h;

1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium in diethyl ether; hexane T=-75°C;

1.1: LDA / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 57 percent / 1,1,2-trichloro-2,2,1-trifluoroethane / tetrahydrofuran; hexane 2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 0.17 h / -75 °C 2.2: 71 percent / tetrahydrofuran; hexane 3.1: 89 percent / H2; ammonium formate / Pd/C / ethanol / 6 h View Scheme

1.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 0.17 h / -75 °C 1.2: 71 percent / tetrahydrofuran; hexane 2.1: 89 percent / H2; ammonium formate / Pd/C / ethanol / 6 h View Scheme

in methanol; hexane; benzene T=20°C; 0.5 h;