Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines.
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 Et(3)N.3HF and NBS.
Verniest
Guido
G
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Piron
Karel
K
Van Hende
Eva
E
Thuring
Jan Willem
JW
Macdonald
Gregor
G
Deroose
Frederik
F
De Kimpe
Norbert
N
D002626:Chemistry, Pharmaceutical; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010880:Piperidines; D011759:Pyrrolidines; D005461:Fluorine