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 |
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Format: | Artikel |
Sprache: | eng |
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•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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2019.151207 |