The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process was written by Nairoukh, Zackaria;Wollenburg, Marco;Schlepphorst, Christoph;Bergander, Klaus;Glorius, Frank. And the article was included in Nature Chemistry in 2019.Formula: C5H11ClFN This article mentions the following:
Piperidines and fluorine substituents are both independently indispensable components in pharmaceuticals, agrochems. and materials. Logically, the incorporation of fluorine atoms into piperidine scaffolds is therefore an area of tremendous potential. However, synthetic approaches towards the formation of these architectures are often impractical. The diastereoselective synthesis of substituted monofluorinated piperidines often requires substrates with pre-defined stereochem. That of multifluorinated piperidines is even more challenging, and often needs to be carried out in multistep syntheses. In this report, we describe a straightforward process for the one-pot rhodium-catalyzed dearomatization-hydrogenation of fluoropyridine precursors. This strategy enables the formation of a plethora of substituted all-cis-(multi)fluorinated piperidines in a highly diastereoselective fashion through pyridine dearomatization followed by complete saturation of the resulting intermediates by hydrogenation. Fluorinated piperidines with defined axial/equatorial orientation of fluorine substituents were successfully applied in the preparation of com. drug analogs. Addnl., fluorinated PipPhos as well as fluorinated ionic liquids were obtained by this dearomatization-hydrogenation process. In the experiment, the researchers used many compounds, for example, 3-Fluoropiperidine hydrochloride (cas: 737000-77-0Formula: C5H11ClFN).
3-Fluoropiperidine hydrochloride (cas: 737000-77-0) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Formula: C5H11ClFN
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem