2-azatricyclo[2.2.1.01,6]heptane: Synthesis and conversion to 2-azabicyclo[2.2.1]heptanes |
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| Authors: | PS Portoghese DT Sepp |
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| Institution: | Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, Minnesota 55455 U.S.A. |
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| Abstract: | A facile route to 6-substituted 2-azabicyclo2.2.1]heptanes via the novel tricyclic system, 2-azatricyclo2.2.1.01,6]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-azabicyclo2.2.1]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. |
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