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Note | Regular issue | Vol 55, No. 11, 2001, pp.2199-2206
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9319
Synthesis of 3-Azabicyclo[3.3.1]nonane-6,9-diones

Brian D. Williams,* Birute Williams, Francis Bernardoni, Robert C. Finn, and Jon Zubieta

*Department of Chemistry, King's College, Wilkes-Barre, Pennsylvania 18711, U.S.A.

Abstract

A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the addition of acryloyl chloride to enamines of N-carboxy-4-piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).