THE CONVERSION OF AMIDES TO ESTERS WITH MEERWEINS REAGENT - APPLICATION TO THE SYNTHESIS OF A CARFENTANIL PRECURSOR

Authors
KIESSLING AJ MCCLURE CK
Citation
Aj. Kiessling et Ck. Mcclure, THE CONVERSION OF AMIDES TO ESTERS WITH MEERWEINS REAGENT - APPLICATION TO THE SYNTHESIS OF A CARFENTANIL PRECURSOR, Synthetic communications, 27(5), 1997, pp. 923-937
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
27
Issue
5
Year of publication
1997
Pages
923 - 937
Database
ISI
SICI code
0039-7911(1997)27:5<923:TCOATE>2.0.ZU;2-D
Abstract
An efficient two step transformation of 1 degrees and 2 degrees amides to methyl and ethyl esters has been developed using trimethyl- and tr iethyloxonium tetrafluoroborates, and dilute acid. This methodology wa s applied to 1-benzyl-4-phenylamino-4-piperidinecarboxamide precursor in the synthesis of carfentanil, to produce the methyl ester in 60% yi eld and the ethyl ester in 80% yield.