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A series of esters derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9a-ol (1) was synthesized and studied by 1 H and 13 C NMR spectroscopy, and the crystal structure of 3-methyl-2,4-diphenyl-9a-(3,5-dimethylbenzoyloxy)-3-azabicyclo[3.3.1]nonane (2) was determined by x-ray diffraction. The compounds studied display in CDCl 3 a preferred flattened chair-chair conformation. This bicycle conformation is similar to that found for 2 in the crystal state. Pharmacological assays on mice were performed to evaluate drug-induced behavioral alteration, peripheral or central acute toxicity and analgesic activity.

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3‐Methyl‐2,4‐diphenyl‐3‐azabicyclo[3.3.1]nonan‐9‐α(β)‐ols have been synthesized and studied by ir, 1H and 13C nmr spectroscopy. In deuteriochloroform and perdeuteriobenzene solutions, these compounds adopt a flattened chair‐chair conformation in which the cyclohexane ring is more flattened. From the 1H and 13C nmr data, several stereoelectronic effects have been deduced. The complete and unambiguous assignment of all protons of the 3‐azabicyclo[3.3.1]nonane system, not described up to date, has been carried out.