title: Synthesis and stereochemical assignment of exo- and endo-7-methyl-7-azabicyclo[2.2.1]heptan-2-ol.
abstract: [formula: see text] The syntheses of both exo and endo stereoisomers of 7-methyl-7-azabicyclo[2.2.1]heptan-2-ol were achieved in straightforward fashion. Alternatively, the intramolecular cyclization of syn-4-N-methylaminocyclohexane 1,2-epoxide was found to give exo-7-methyl-7-azabicyclo-[2.2.1]heptan-2-ol as the sole product. The stereochemistry of the exo isomer was unequivocally confirmed by X-ray crystallography.
authors.affiliation: Department of Chemistry, University of New Orleans, Louisiana 70148, USA.
authors.forename: K C
authors.initials: KC
authors.lastname: Ramanaiah
authors.forename: N
authors.initials: N
authors.lastname: Zhu
authors.forename: C
authors.initials: C
authors.lastname: Klein-Stevens
authors.forename: M L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D013237:Stereoisomerism
chemical_list: C409083:7-methyl-7-azabicyclo(2.2.1)heptan-2-ol; D019086:Bridged Bicyclo Compounds, Heterocyclic