The Conversion of Amides to Esters with Meerwein'S Reagent. Application to the Synthesis of a Carfentanil Precursor.
- 1 March 1997
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 27 (5) , 923-937
- https://doi.org/10.1080/00397919708004212
Abstract
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.Keywords
This publication has 19 references indexed in Scilit:
- Amide to ester conversion: a practical route to the carfentanil class of analgeticsThe Journal of Organic Chemistry, 1992
- A novel route to the 4-anilido-4-(methoxycarbonyl)piperidine class of analgeticsThe Journal of Organic Chemistry, 1990
- 4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agentsJournal of Medicinal Chemistry, 1989
- Synthesis and pharmacological evaluation of 4,4-disubstituted piperidinesJournal of Medicinal Chemistry, 1989
- New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist propertiesJournal of Medicinal Chemistry, 1989
- Simultaneous determination of fentanyl and its major metabolites and fentanyl analogues using gas chromatography and nitrogen-selective detectionJournal of Chromatography B: Biomedical Sciences and Applications, 1989
- Structure-Activity Studies of FentanylJournal of Pharmacy and Pharmacology, 1988
- Synthetic 1,4-disubstituted 1,4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: Alfentanil (R 39209), a potent, extremely short-acting narcotic analgesicJournal of Medicinal Chemistry, 1986
- Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-[3-methyl-1-(2-phenylethyl)-4-piperidyl]-N-phenylpropanamide and N-[3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl]-N-phenylpropanamideJournal of Medicinal Chemistry, 1974
- Synthetic studies on tetrodotoxin and related compounds. IV. Stereospecific total syntheses of DL-tetrodotoxinJournal of the American Chemical Society, 1972