Abstract
Abstractd, l‐Glaucine 1.5 H3PO4, is a non‐narcotic antitussive for which a sample of carbon‐13 labelled material was required for metabolism studies in humans. The sample of 99% enriched d, l‐6a‐13C‐glaucine 1.5 H3PO4 was prepared in 7 steps in 36% overall yield starting with purchased 99% enriched 1‐13C‐papaverine. The papaverine was N‐methylated with methyl iodide and the resulting methiodide reduced to d, l‐1‐13C‐laudanosine with sodium borohydride. The laudanosine was O‐demethylated with 48% HBr and cyclized to d, l‐6a‐13C‐1,2,9,10‐tetrahydroxyaporphine (THA) using aqueous ferric chloride/sodium acetate and isolated as the hydrochloride salt (THA ± HCl). The THA ± HCl was converted to the free base and remethylated with phenyltrimethylammonium hydroxide. The resulting d, l‐6a‐13C‐glaucine was purified by column chromatography and isolated as the hydrobromide salt. The d, l‐6a‐13C‐glaucine 1.5 H3PO4 was obtained by conversion of the hydrobromide to the free base and treatment with 85% phosphoric acid in ethanol.
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