title: Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.
abstract: 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 (1)H NMR monitoring. The relative and absolute stereochemistry of all four stereoisomers was determined by a combination of (1)H, (13)C, and (15)N NMR spectroscopy and vibrational circular dichroism spectroscopy.
authors.affiliation: Discovery Analytical Chemistry, Chemical and Screening Sciences, Wyeth Research, Collegeville, Pennsylvania 19426, USA. goljeri@wyeth.com
authors.forename: Igor
authors.initials: I
authors.lastname: Goljer
authors.forename: Albert
authors.initials: A
authors.lastname: Molinari
authors.forename: Yanan
authors.initials: Y
authors.lastname: He
authors.forename: Lisa
authors.initials: L
authors.lastname: Nogle
authors.forename: Weilin
authors.initials: W
authors.lastname: Sun
authors.forename: Brandon
authors.initials: B
authors.lastname: Campbell
authors.forename: Oliver
authors.initials: O
authors.lastname: McConnell