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8.2.2.3 Method 3: Alkylation of Amines and Amides

DOI: 10.1055/sos-SD-008-00607

Venturello, P.; Barbero, M.Science of Synthesis, (20068900.

Regioselective N-alkylation of different heterocycles has been achieved using sodium hydride in the presence of various electrophiles. Methyl and ethyl indole-2-carboxylates,[‌14‌,‌15‌] heterocyclic ketene aminals,[‌16‌,‌17‌] 6-substituted pyridin-2-ones,[‌18‌] and optically active 4,5-dihydro-1,2,4-triazin-6(1H)-ones[‌19‌] have been alkylated using sodium hydride in dimethylformamide or 1,2-dimethoxyethane/dimethylformamide. Reaction of imidazolidine 16 with sodium hydride followed by bromoacetate gives alkylated products 17 (Table 1).

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MMM, ee 88 [‌88‌]
MMM, 88°M 8888e [‌88‌]
MMM/MMM (8:8), 8°M 88 [‌88‌]
MMM/MMM (8:8), 8°M 88 [‌88‌]
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References