Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines

Literature Information

Publication Date 2010-04-21
DOI 10.1039/C003380D
Impact Factor 3.876
Authors

Guido Verniest, Karel Piron, Eva Van Hende, Jan Willem Thuring, Gregor Macdonald, Frederik Deroose, Norbert De Kimpe


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Abstract

A short and efficient synthesis of 4-aminomethyl-4-fluoropiperidines and 3-aminomethyl-3-fluoropyrrolidines is described. These fluorinated azaheterocycles are of specific interest as bifunctional building blocks for fluorinated pharmaceutical compounds. The key step of the synthetic pathway involves the regioselective bromofluorination of N-Boc-4-methylenepiperidine and 3-methylenepyrrolidine using Et3N.3HF and NBS.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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