Unexpected Rearrangement of Enantiomerically Pure 3-Aminoquinuclidine as a Simple Way of Preparing Diastereomeric Octahydropyrrolo[2,3-c]pyridine Derivatives

摘要

Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient way of generating stereochemically defined isomers. Optimization of reaction conditions was carried out by H-1 NMR monitoring. The relative and absolute stereochemistry of all four stereoisomers was determined by a combination of H-1, C-13 and N-15 NMR spectroscopy and vibrational circular dichroism spectroscopy.