Tetrahedron Letters p. 1297 - 1300 (1996)
Update date:2022-09-26
Topics:
Taylor, G. Mark
Baker, Stewart J.
Gedney, Andrea
Pearson, David J.
Sibley, Graham E. M.
The Ritter reactions of 3-alkyl-3-hydroxyazetidine or -piperidine derivatives give low yields of the desired products, whereas the 3-alkyl-3-hydroxy-pyrrolidine and 4-alkyl-4-hydroxy-piperidine derivatives react smoothly to give the corresponding acetamides. An alternative route to 3-acylamino-3-alkylpiperidines, which were designed as conformationally-restricted reduced amide dipeptide isosteres, was devised from nipecotic acid vai a Hofmann rearrangement.
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