Bicyclic Bases. Synthesis of 2,5-Diazabicyclo[2.2.1]heptanes

Philip S. Portoghese, Adel A. Mikhail

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A route to the novel bicyclic system, 2,5-diazabicyclo[2.2.1]heptane, has been elaborated. The starting material, hydroxy-L-proline, was transformed to tritosylhydroxy-L-prolinol, which was then cyclized to 2-tosyl-5-benzyl-2,5-diazabicyclo[2.2.1]heptane with benzylamine. The latter structure was subsequently converted to the parent bicyclic system. Some of the reaction mechanisms leading to the bicyclio compound are discussed, and the nmr spectra of the title compound and its ditosyl derivative are interpreted.

Original languageEnglish (US)
Pages (from-to)1059-1062
Number of pages4
JournalJournal of Organic Chemistry
Issue number4
StatePublished - Apr 1 1966


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