N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) THF, 1 h, 2.) THF, RT, overnight; Yield given. Multistep reaction;

1: 1.) sec-butyllithium, TMEDA / 1.) THF, 1 h, 2.) THF, RT, overnight 2: 74 percent / H2 / 10percent palladium/charcoal / ethyl acetate / 24 h / 2585.7 Torr / Ambient temperature View Scheme

Yield given. Multistep reaction;

1: 1.) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h 2: 1.) MeI, 2.) 10percent aq. NaOH / 1.) THF, reflux, 4 h, 2.) THF, reflux, 7 h 3: 90 percent / 10percent aq. HCl / 4 h / Heating View Scheme