Yokoyama N, Almaula P I, Block F B, Granat F R, Gottfried N, Hill R T, McMahon E H, Munch W F, Rachlin H, Saelens J K, Siegel M G, Tomaselli H C, Clarke F H
J Med Chem. 1979 May;22(5):537-53. doi: 10.1021/jm00191a016.
The synthesis, analgetic activity, and physical dependence capacity of a large number of 5-phenyl-6,7-benzomorphan derivatives are described. Observations made during the Stevens' rearrangement of 1-benzyl-1-methyl-delta 3-piperidinium salt derivatives (V) under various conditions are discussed. The absolute configuration of the 9-demethyl series and the 2'-deoxy series is established by comparison of their ORD and CD spectra with those of 49, whose absolute configuration was previously established by X-ray crystallography. A convenient synthesis of 3H-labeled phenols using 3H3PO4 is described, as well as the preparation of 14C-labeled compounds by conventional methods.
