Issue 11, 2010

Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines

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.

Graphical abstract: Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines

Supplementary files

Article information

Article type
Communication
Submitted
22 Feb 2010
Accepted
06 Apr 2010
First published
21 Apr 2010

Org. Biomol. Chem., 2010,8, 2509-2512

Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines

G. Verniest, K. Piron, E. Van Hende, J. W. Thuring, G. Macdonald, F. Deroose and N. De Kimpe, Org. Biomol. Chem., 2010, 8, 2509 DOI: 10.1039/C003380D

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