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General methods for the preparation of deuterium and tritium‐labelled phenethylamines and phenethanollamines: Synthesis of radioactive 6‐hydroxydopamine
Author(s) -
Rotman A.,
Daly J. W.,
Creveling C. R.
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110320
Subject(s) - nitroethane , chemistry , nitromethane , tritium , phenethylamines , sodium cyanoborohydride , methylamines , deuterium , ketone , nitro , organic chemistry , radiochemistry , medicinal chemistry , stereochemistry , physics , alkyl , quantum mechanics , nuclear physics , catalysis
A convenient synthetic method for preparation of phenethylamines and phenethanolamines labeled with deuterium or tritium has been developed. A substituted benzaldedyde is condensed with nitromethane or nitroethane and the resultant nitrostyrene is reduced with sodium borotritide or borodeuteride. Subsequent reduction of the nitro‐group and removal of blocking groups yields a phenethylamine or an a‐methylphenethylamine containing a tritium or deuterium in the benzylic position. Condensation of the substituted benzaldehyde with nitromethane or nitroethane at low temperature yields a nitroalcohol which is oxidized to a ketone with Jones reagent. Reduction with sodium borotritide or borodeuteride and subsequent reduation of the nitro‐group and removal of blocking groups yields a phenethanolamine or α‐methylphenethanolamine labeled in the bensylic position. Preparation of deutero‐ and/or tritio‐labeled 2,4,5‐trihydroxyphenethylamine (6‐hydroxydopamine). α‐methyl‐6‐hydroxydopamine, α‐methyl‐ p ‐tyramine, β‐phenethanolamine. 2‐hydroxyphenethanolamine and α‐methyl‐4‐benzyloxyphenethanolamine is described.