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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.

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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:18 Apr 2018 11:41
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds (SNF), F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.201000370
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSchweizerischer Nationalfonds (SNF)
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

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