Organic and Biomolecular Chemistry, volume 8, issue 11, pages 2509
Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines
Guido Verniest
1
,
Karel Piron
1
,
Eva Van Hende
1
,
Jan Willem Thuring
2
,
Gregor Macdonald
2
,
Frederik Deroose
2
,
Norbert De Kimpe
1
2
Johnson & Johnson, Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica NV, Turnhoutseweg 30, B-2340 Beerse, Belgium
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Publication type: Journal Article
Publication date: 2010-04-21
Journal:
Organic and Biomolecular Chemistry
scimago Q2
SJR: 0.607
CiteScore: 5.5
Impact factor: 2.9
ISSN: 14770520, 14770539
DOI:
10.1039/c003380d
PubMed ID:
20407687
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
Found
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