New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides

[Display omitted] •Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should prov...

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Veröffentlicht in:Tetrahedron letters 2019-10, Vol.60 (44), p.151207, Article 151207
Hauptverfasser: Babić, Nikola, Peyrot, Fabienne
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should provide cheaper 15N-labelled probes. A new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one and derived aminoxyl (nitroxide) radicals is described. In this preliminary work, 2,2,6,6-tetraethylpiperidin-4-one was obtained from ethyl acetoacetate in 3% yield over eight steps, relying only on common reagents and laboratory equipment for organic synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151207