A facile synthesis of octahydro-pyrrolo[2,3-c]pyridine 1 usingan intramolecular [3+2]-cycloaddition of an azomethine ylideas the key step and employing DW-therm heat-transfer fluidas a solvent is disclosed. Enantiomerically pure 1 was obtainedeither via a chromatographic separation of the diastereoisomers12 and 13 resulting from the cycloaddition with a chiralappendage or by a classical resolution of racemate 19.