DPP-IV inhibitors have been suggested as potential new treatments for type-II diabetes and 2-cyanopyrrolidides have been reported as potent DPP-IV inhibitors. Alternative synthetic approaches to one such compound, NVP-DPP728, are investigated here. One strategy is based in solution phase and is amenable to scale-up. The other is based on solid phase and is appropriate for the rapid analoging of the structural series.