Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine |
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Authors: | Shengyin Zhao |
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Affiliation: | Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA |
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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 6 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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Keywords: | Rearrangement Piperidone Pyrrolidone Clemmensen reduction |
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