Generation of secondary alkyl amines on solid support by borane reduction: Application to the parallel synthesis of PPAR ligands

Article abstract of DOI:10.1055/s-1997-1415

A solid phase parallel synthesis of fibrate PPAR ligands 1 has been developed. The key reaction is a novel borane reduction of resin bound amides that generates secondary amines not accessible by inductive alkylation of primary amines. The FMOC-protected amino-fibrate 2 was loaded onto Sasrin resin via the carboxylic acid. The amine was elaborated by amide bond formation followed by reduction with borane. The resulting secondary amines reacted with aryl isocyanates to generate the fibrates 1 in high yield and purity following cleavage from the solid support.