Abstract
The stereochemistry of optically active α- and β-methadol has been deduced by the asymmetric synthetic procedure of Prelog. The apparent dissociation constants of the title compounds, when compared with those of methadone and 3-deoxymethadone, suggest the absence of substantial intramolecular H bonding in aqueous medium. Nmr and ir studies point to the presence of strong intramolecular H bonds in nonpolar media, with the β isomer being more strongly internally associated. Possible preferred conformations which are consistent with the spectral data are depicted. The (6R), (6S), and (6R) receptor stereoselectivities for methadone, α-methadol, and acetyl-α-methadol, respectively, have been rationalized in terms of differing modes of interaction.
Original language | English (US) |
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Pages (from-to) | 839-844 |
Number of pages | 6 |
Journal | Journal of medicinal chemistry |
Volume | 12 |
Issue number | 5 |
DOIs | |
State | Published - Sep 1 1969 |
Externally published | Yes |