The conversion of amides to esters with Meerwein's reagent. Application to the synthesis of a carfentanil precursor

Article abstract of DOI:10.1080/00397919708004212

An efficient two step transformation of 1°and 2°amides to methyl and ethyl esters has been developed using trimethyl- and triethyloxonium tetrafluoroborates, and dilute acid. This methodology was applied to 1-benzyl-4-phenylamino-4-piperidinecarboxamide, a precursor in the synthesis of carfentanil, to produce the methyl ester in 60% yield and the ethyl ester in 80% yield.

Full text of DOI:10.1080/00397919708004212

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The Conversion of Amides
to Esters with Meerwein'S
Reagent. Application to the
Synthesis of a Carfentanil
Precursor.
Anthony J. Kiessling a & Cynthia K. McClure a
a Department of Chemistry and Biochemistry,
University of Delaware, Newark, Delaware,
19716
Version of record first published: 22 Aug 2006.
To cite this article: Anthony J. Kiessling & Cynthia K. McClure (1997): The
Conversion of Amides to Esters with Meerwein'S Reagent. Application to the
Synthesis of a Carfentanil Precursor., Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 27:5, 923-937
To link to this article: http://dx.doi.org/10.1080/00397919708004212
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