Abstract
The syntheses of the antidepressant drug, amitriptyline, and its metabolites nortriptyline and desmethylnortriptyline, doubly labelled with carbon-13 have been accomplished in thirteen stages. Ba13CO3 was used for the carbonation of o-tolylmagnesium bromide, which subsequently provided a 13C-label distributed between positions 5, 10 and 11 in the tricyclic ring. A second carbon-13 atom was introduced at the terminal side-chain carbon, adjacent to nitrogen, using Na13CN.
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