Preparation of Resin-BoundN-(α-Methoxyalkyl)amides: An Advantageous Use of Solid-Phase Chemistry for the Handling of Unstable Precursors of the VersatileN-Acyliminium Ions
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