Synthesis and stereochemical assignment of exo- and endo-7-methyl-7-azabicyclo[2.2.1]heptan-2-ol.
[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.
Ramanaiah
K C
KC
Department of Chemistry, University of New Orleans, Louisiana 70148, USA.
Zhu
N
N
Klein-Stevens
C
C
Trudell
M L
ML
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D013237:Stereoisomerism
C409083:7-methyl-7-azabicyclo(2.2.1)heptan-2-ol; D019086:Bridged Bicyclo Compounds, Heterocyclic