Header

UZH-Logo

Maintenance Infos

Reactions with 4-Hydroxy-2-methylbutananilides – unexpected formation of a cyclopropanecarboxamide


Heimgartner, H; Linden, A; Mekhael, M K G (2011). Reactions with 4-Hydroxy-2-methylbutananilides – unexpected formation of a cyclopropanecarboxamide. Helvetica Chimica Acta, 94(1):28-37.

Abstract

The successive treatment of the N,N-disubstituted 4-hydroxy-2-methylbutanamide 2a with 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.

Abstract

The successive treatment of the N,N-disubstituted 4-hydroxy-2-methylbutanamide 2a with 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.

Statistics

Altmetrics

Downloads

105 downloads since deposited on 08 Feb 2011
10 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:January 2011
Deposited On:08 Feb 2011 16:38
Last Modified:21 Nov 2017 15:15
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds (SNF), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201000370

Download