Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives |
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Authors: | Goljer Igor Molinari Albert He Yanan Nogle Lisa Sun Weilin Campbell Brandon McConnell Oliver |
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Institution: | Discovery Analytical Chemistry, Chemical and Screening Sciences, Wyeth Research, Collegeville, Pennsylvania 19426, USA. goljeri@wyeth.com |
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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 octahydropyrrolo2,3]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. |
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Keywords: | 3‐aminoquinucldine octahydropyrrolo[2 3‐c]pyridine rearrangement |
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