Preparation of resin-bound N-(alpha-methoxyalkyl)amides: an advantageous use of solid-phase chemistry for the handling of unstable precursors of the versatile N-acyliminium ions.

Abstract

The development of a new and efficient synthesis of resin-bound N-(alpha-methoxyalkyl)amides is described. The condensation of aldehydes on a supported amide in the presence of trimethyl orthoformate afforded, in acidic media, the resin-bound N-acyliminium ion precursors. Repeating the reaction a second time led to a great improvement in yields, demonstrating one advantage of the solid-phase chemistry for the handling of sensitive intermediates difficult to isolate.