Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid phase synthesis of N-substituted amide derivatives

Brown, E., G.; Nuss, J., M.

Tetrahedron Letters 38(49): 8457-8460

1997


ISSN/ISBN: 0040-4039
DOI: 10.1016/s0040-4039(97)10279-9
Accession: 008125445

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Abstract
Reductive amination of aldehydes and ketones using sodium cyanoborohydride and Rink's 4-(2',4'-dimethoxyphenyl-aminomethyl)-phenoxymethyl-linked polystyrene resin (Rink's amine linker on co-poly-(styrene-1%-divinylbenzene)) 2 affords high yields of linker-bound, N-alkyl amines with excellent chemical selectivity. Subsequent coupling with acid derivatives gave derivatized N-substituted amides in excellent yields after cleavage from the solid-support.