A facile synthesis of [14C]enadoline [(5R)-(5α, 7α,8β)]-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5] DEC-8-YL]-4-benzofuranacetamide

A facile synthesis of [14C]enadoline [(5R)-(5α, 7α,8β)]-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5] DEC-8-YL]-4-benzofuranacetamide

4‐Chloromethylbenzofuran (10) was synthesized from 2,3‐dimethylanisole in 7 steps. The corresponding Grignard reagent prepared from magnesium‐anthracene complex reacts with 14CO2, SOCl2, and PD130812 successively to give [14C]enadoline (2), a non‐peptide, selective kappa opioid receptor agonist. Thi...

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Veröffentlicht in:Journal of labelled compounds & radiopharmaceuticals 1995-12, Vol.36 (12), p.1183-1191
Hauptverfasser: Pu, Yu-Ming, Scripko, James, Huang, Che C.
Format: Artikel
Sprache:eng
Schlagworte:
Analgesic
C-14 Label
Chemistry
Enadoline
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Opioid Receptors
Organic chemistry
Preparations and properties
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Zusammenfassung:4‐Chloromethylbenzofuran (10) was synthesized from 2,3‐dimethylanisole in 7 steps. The corresponding Grignard reagent prepared from magnesium‐anthracene complex reacts with 14CO2, SOCl2, and PD130812 successively to give [14C]enadoline (2), a non‐peptide, selective kappa opioid receptor agonist. This method could be readily modified for the rapid, one‐pot synthesis of [11C]enadoline.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.2580361208