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d , l ‐6a‐ 13 C‐Glaucine 1.5 phosphate
Author(s) -
Henton Daniel R.,
Goralski Christian T.,
Heeschen Jerry P.,
Nyquist Richard A.,
Pfeiffer Curtis D.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270308
Subject(s) - chemistry , hydrobromide , nuclear chemistry , methiodide , hydrochloride , chromatography , stereochemistry , organic chemistry
d , l ‐Glaucine 1.5 H 3 PO 4 , 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‐ 13 C‐glaucine 1.5 H 3 PO 4 was prepared in 7 steps in 36% overall yield starting with purchased 99% enriched 1‐ 13 C‐papaverine. The papaverine was N‐methylated with methyl iodide and the resulting methiodide reduced to d , l ‐ 1 ‐ 13 C‐laudanosine with sodium borohydride. The laudanosine was O‐demethylated with 48% HBr and cyclized to d , l ‐6a‐ 13 C‐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‐ 13 C‐glaucine was purified by column chromatography and isolated as the hydrobromide salt. The d , l ‐6a‐ 13 C‐glaucine 1.5 H 3 PO 4 was obtained by conversion of the hydrobromide to the free base and treatment with 85% phosphoric acid in ethanol.