Synthesis of N-(α-Methoxyalkyl) Amides from Imidates

Article abstract of DOI:10.1021/jo00350a035

Two general routes from imidates to N-(α-methoxyalkyl) amides (e.g.,R'CONHCH(OCH3)R, 1) are reported.The first involves acylation of the imidate on nitrogen with an acyl chloride, followed by reduction with sodium borohydride.In the second, an aldehyde is converted, via its methyl acetal, to an α-chloro methyl ether, which is used to alkylate the imdate.Further treatment with pyridinium chloride in dry Me2SO yields 1.Thirteen examples are reported.