| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5226136 | Tetrahedron | 2006 | 9 Pages |
Abstract
We report that 1-benzyl-2-methyl-3-piperidone, conveniently prepared from 3-hydroxy-2-methylpyridine, undergoes rearrangement to 1-benzyl-2-acetylpyrrolidine in aqueous 6Â N HCl at reflux. Studies showing that the 2,2-dimethyl analog is inert under the same conditions support a mechanism of reversible tautomeric equilibria via ring-opened intermediates, one of which was independently synthesized and shown to be a kinetically competent intermediate to product.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Shengyin Zhao, Heung-Bae Jeon, Durgesh V. Nadkarni, Lawrence M. Sayre,