Acid mediated deprotection of N-isopropyl tertiary amides. Issue 10 (4th March 2015)

• Record Type: Journal Article
• Authors: Lorenc, Chris; Reeves, Jonathan T.; Busacca, Carl A.; Senanayake, Chris H.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 10(2015)
• Page Start: 1280
• Page End: 1282
• Publication Date: 2015-03-04
• Subjects: Amides -- Acid -- Deprotection -- Dealkylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.161
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Tertiary amides containing an N -isopropyl group were selectively deprotected by heating in methanesulfonic acid. The N -isopropyl group was removed selectively in the presence of other groups on the amide nitrogen such as methyl, primary alkyl, or aryl. The putative isopropyl cation was trapped by Friedel–Crafts alkylation of anisole when the latter was included as a co-solvent.