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Report | Regular issue | Vol 24, No. 12, 1986, pp.3373-3377
Published online, 1st January, 1970
DOI: 10.3987/R-1986-12-3373
A Useful Construction of 4-Substiotuted 1-Alkylpiperid-3-ones

Charles S. Swindell* and Ruth H. Duffy

*Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA 19010, U.S.A.


A potentially general construction of 4-substituted 1-alkylpiperid-3-ones is described which employs 3-methoxy-4-bromopyridine as the crucial reagent. This substance is coupled at C-4 with Grignard reagents through the Kumada reaction. The resulting pyridines are then N-alkylated and subsequently subjected to borohydride reduction and aqueous acidic hydrolysis to reveal the title piperidones and related substances.