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General methods for the preparation of deuterium and tritium-labelled phenethylamines and phenethanollamines: Synthesis of radioactive 6-hydroxydopamine

1975; Wiley; Volume: 11; Issue: 3 Linguagem: Inglês

10.1002/jlcr.2590110320

1559-0860

Avner Rotman, John W. Daly, Cyrus R. Creveling,

Boron Compounds in Chemistry

Abstract 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.