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DOI: 10.1055/s-0029-1217360
Synthesis of 3-Aminomethyl-3-fluoropiperidines
Publikationsverlauf
Publikationsdatum:
12. Juni 2009 (online)
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Abstract
A synthetic route toward new 1-alkyl-3-aminomethyl-3-fluoropiperidines, which are of high interest as building blocks in medicinal chemistry, is described. The successful approach consists of the fluorination of ethyl 3-chloropropyl-2-cyanoacetate with N-fluorodibenzenesulfonimide (NFSI) and transformation of the ester moiety into different amides, yielding N-alkyl-5-chloro-2-cyano-2-fluoropentanamides. Ring closure was achieved under basic conditions, yielding 1-alkyl-3-fluoro-2-oxopiperidine-3-carbonitriles. After reduction of the obtained lactams with borane, the desired 3-aminomethyl-3-fluoropiperidines were obtained in good yields.
Key words
ring closure - NFSI - 3-fluoropiperidines - fluorine chemistry - heterocycles
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References and Notes
Postdoctoral Fellow of the Research Foundation - Flanders (FWO-Vlaanderen)