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An efficient synthesis of (R)- and (S)-2-(aminomethyl)piperidine dihydrochloride

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
19
Issue
19
Identifiers
DOI: 10.1016/j.tetasy.2008.09.015
Disciplines
  • Pharmacology

Abstract

Abstract The synthesis of the dihydrochloride salts of ( R)- 1 and ( S)- 1 2-(aminomethyl)piperidine is reported starting from either ( S) or ( R) lysine, respectively. A key step in the synthetic protocol involves the in situ formation of aziridinium 8, which then undergoes an intramolecular ring opening with concomitant piperidinium ring formation, in a stereoselective manner. The route offers a practical synthesis of ( R)- 1 and ( S)- 1, and it should make them more accessible for exploration in asymmetric catalysis or as building blocks in pharmaceutical research.

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