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Synthesis of R ‐[ N ‐methyl‐ 13 C]SKF 82957 from [ 13 C]methyl iodide and [ 13 C]methyl triflate
Author(s) -
Dasilva Jean N.,
Burrow Timothy E.,
Wilson Alan A.,
Houle Sylvain
Publication year - 2000
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 - 10.1002/1099-1344(200006)43:7<701::aid-jlcr355>3.0.co;2-w
Subject(s) - chemistry , carbon 13 nmr , methyl iodide , trifluoromethanesulfonate , desmethyl , medicinal chemistry , stereochemistry , organic chemistry , catalysis , metabolite , biochemistry
With the aim to establish the labeling position in the radiosynthesis of the dopamine D 1 agonist R ‐[ 11/13 C]SKF 82957, reaction mixtures containing R ‐SKF 81297, N ‐ethyldiisopropylamine, and [ 13 C]methyl oidide or [ 13 C]methyl triflate, were analyzed using 1 H‐ and 13 C‐NMR, as well as 2D 1 H‐ 13 C‐NMR. Only R ‐[ N ‐ methyl ‐ 13 C]SKF 82957 was obtained using sub‐molar quantities of [ 13 C]methyl iodide. In contrast, a second 13 C‐labeled peak, likely corresponding to an O ‐[ 13 C]methylated derivative, was observed with the highly reactive [ 13 C]methyl triflate. Similar results were obtained in the synthesis of the structurally similar R ‐[ 13 C]SCH 23390. Copyright © 2000 John Wiley & Sons, Ltd.