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d,l-6a-13C-Glaucine 1.5 phosphate

✍ Scribed by Daniel R. Henton; Christian T. Goralski; Jerry P. Heeschen; Richard A. Nyquist; Curtis D. Pfeiffer

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
471 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

d,l--Glaucine 1.5 H3P04 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 ci,L-Ba-C-glaucine 1.5 H3P04 was prepared in 7 steps in 36% overall yield starting with purchased 99% enriched 1-The papaverine was N-methylated with methyl iodide and the resulting methiodide reduced to g,l-l-C-laudanosine with sodium borohydride. The laudanosine was 0 -d e m e t h y l a t e d w i t h 4 8 % H B r a n d c y c l i z e d t o d , A -6 a -1 3 C -1,2,9,10-tetrahydroxyaporphine (THA) using aqueous ferric chloride/sodium acetate and isolated as the hydrochloride salt (THA'HC1).

The THA'HC1 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-C-glaucine 1.5 H3P04 was obtained by conversion of the hydrobromide to the free base and treatment with 85% phosphoric acid in ethanol.

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