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

JP Lokensgard, JW Fischer, WJ Bartz…

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

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被引用次数: 13

摘要

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.