Synthesis of N-(. alpha.-methoxyalkyl) amides from imidates

JP Lokensgard, JW Fischer, WJ Bartz…

Index: Lokensgard, Jerrold P.; Fischer, John W.; Bartz, William J. Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5609 - 5611

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Citation Number: 13

Abstract

Two general routes from imidates to N-(a-methoxyalkyl) amides (eg, R'CONHCH (OCH,) 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 a-chloro methyl ether, which is used to alkylate the imidate. Further treatment with pyridinium chloride in dry MezSO yields 1. Thirteen examples are reported.