title: 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 Et(3)N.3HF and NBS.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest
authors.forename: Karel
authors.initials: K
authors.lastname: Piron
authors.forename: Eva
authors.initials: E
authors.lastname: Van Hende
authors.forename: Jan Willem
authors.initials: JW
authors.lastname: Thuring
authors.forename: Gregor
authors.initials: G
authors.lastname: Macdonald
authors.forename: Frederik
authors.initials: F
authors.lastname: Deroose
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: 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
chemical_list: D010880:Piperidines; D011759:Pyrrolidines; D005461:Fluorine