Abstract
The conformational preferences of α(I) and β(II) epimers of 3-phenethyl-3-azabicyclo[3.3.1]nonan-9-ol, have been studied using the molecular mechanics method (MM2 and MM2′ programs). In both cases, the global minimum-energy conformer computed correspond to a slightly flattened CC conformation with the 3N-phenethyl group in the β-position. This behaviour is in agreement with the conformation adopted in solution in polar solvents. In relation to the energy differences between N-axial and N-equatorial conformations, these epimers exhibit an intermediate situation between the tropine and the α and β epimers of 3-phenethyl-3-azabicyclo[3.2.1]octan-8-ol.
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