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Reactions with 4-Hydroxy-2-methylbutananilides: Unexpected Formation of a Cyclopropanecarboxamide

✍ Scribed by Maged K. G. Mekhael; Anthony Linden; Heinz Heimgartner

Publisher: John Wiley and Sons
Year: 2011
Tongue: German
Weight: 197 KB
Volume: 94
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.201000370

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✦ Synopsis

Abstract

The successive treatment of the N,N‐disubstituted 4‐hydroxy‐2‐methylbutanamide 2a with lithium diisopropylamide (LDA) and diphenyl phosphorochloridate (DPPCl) led to the 1‐methylcyclopropanecarboxamide 10 in good yield. This base‐catalyzed cyclization offers a new approach to cyclopropanecarboxamides. Under similar conditions, the N‐monosubstituted 4‐hydroxy‐2‐methylbutanamide 2b gave the 3‐methylpyrrolidin‐2‐one 11. The structure of the cyclopropanecarboxamide 10 was established by X‐ray crystallography.

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