Quick access to optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine

doi:10.1055/S-2006-926306

Paper

Quick access to optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine

Published Feb 1, 2006 · J. Ruano, J. Alemán, M. Cid

Synthesis

Q2 SJR score

21

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0

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Abstract

Optically pure 2-(l-hydroxybenzyl)piperidine and pyrrolidine were prepared by reaction of oxygenated 2-(p-tolylsulfinyl)benzyl carbanions with the appropriate chlorinated N-sulfinylimines followed by subsequent elimination of the sulfinyl groups. The main reaction is a tandem process involving nucleophilic addition of the sulfinylbenzyl carbanion to the C=N bond followed by intramolecular elimination of the chlorine by the resulting amide. The matched pair of the reagents (exhibiting the same configuration at their respective sulfinyl moieties) evolves with a complete control of the stereoselectivity at the two newly created chiral carbons.

Study Snapshot

This study provides a quick access to optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine, enabling their use in various applications.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Quick access to optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine

References

Citations

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