2-azatricyclo[2.2.1.01,6]heptane: Synthesis and conversion to 2-azabicyclo[2.2.1]heptanes

P. S. Portoghese, D. T. Sepp

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Abstract

A facile route to 6-substituted 2-azabicyclo[2.2.1]heptanes via the novel tricyclic system, 2-azatricyclo[2.2.1.01,6]heptane (2), is described. The key intermediate (2) was prepared by oxidation of 4-aminomethylcyclopentene with lead tetra-acetate, and the bicyclic system was obtained by reaction of acetate with 2.MeI. Equilibration of exo- and endo-6-hydroxy-1-methyl-2-azabicyclo[2.2.1]heptane afforded an exo-endo isomeric ratio close to that of norborneol, and on this basis it is suggested that the steric requirements of the nitrogen lone pair are similar to that of CH.

Original languageEnglish (US)
Pages (from-to)2253-2256
Number of pages4
JournalTetrahedron
Volume29
Issue number15
DOIs
StatePublished - 1973

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