901279-68-3Relevant academic research and scientific papers
Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine
Zhao, Shengyin,Jeon, Heung-Bae,Nadkarni, Durgesh V.,Sayre, Lawrence M.
, p. 6361 - 6369 (2007/10/03)
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.
