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21.10.1.1.3.1.4.2 Variation 2: By Reductive Alkylation of Lactams with Aldehydes

DOI: 10.1055/sos-SD-021-00600

Smith, M. B.Science of Synthesis, (200521688.

Lactams can be reductively alkylated by reaction with aldehydes under catalytic-hydrogenation conditions. The initial reaction with the lactam nitrogen generates an iminium intermediate that is hydrogenated to give the N-alkyl derivative. For example, treatment of pyrrolidin-2-one (128) with butanal and hydrogen gas in the presence of a palladium on carbon at 100°C gives a 98% yield of 1-butylpyrrolidin-2-one (134) (Scheme 60).[‌173‌]

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