Title: Synthesis of 3-substituted pyrrolidin-2-ones and 3-substituted piperidin-2-ones from esters.
Authors: Brunotte, Lara; Beckmann, Lars; Ljiljanic, Marko; Opatz, Till
Abstract: δ-Lactams and 1-lactams present important structural moieties which are found in many pharmaceuticals, targeting a wide array of diseases. Starting from commercially available esters, we developed a facile method for the synthesis of 3-substituted pyrrolidin-2-ones and piperidin-2-ones. To this end, the ester is a-alkylated with 2-azidoethyl trifluoromethanesulfonate or 2-azidopropyl trifluoromethanesulfonate, followed by azide reduction and ring closure. A continuous flow protocol was developed for the azide - amine transformation but a batch protocol is available as well.
Subjects: ESTERS; MOIETIES (Chemistry); AMINES; DRUGS
Publication: ARKIVOC: Online Journal of Organic Chemistry, 2024, Vol 2024, p1
ISSN: 1551-7004
Publication type: Academic Journal
DOI: 10.24820/ark.5550190.p012.235

Synthesis of 3-substituted pyrrolidin-2-ones and 3-substituted piperidin-2-ones from esters.

Brunotte, Lara; Beckmann, Lars; Ljiljanic, Marko; Opatz, Till