Dielectrically controlled resolution (DCR) of 3-aminopiperidine via diastereomeric salt formation with N-tosyl-(S)-phenylalanine

Rumiko Sakurai,Kenichi Sakai,Koichi Kodama,Masanori Yamaura

doi:10.1016/j.tetasy.2012.02.002

Dielectrically controlled resolution (DCR) of 3-aminopiperidine via diastereomeric salt formation with N-tosyl-(S)-phenylalanine

Rumiko Sakurai, Kenichi Sakai + Show 2 more

https://doi.org/10.1016/j.tetasy.2012.02.002

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Journal: Tetrahedron: Asymmetry	Publication Date: Feb 1, 2012
Citations: 16

Affiliation: Iwaki Meisei University, Saitama University

#Less-soluble Diastereomeric Salt #Diastereomeric Salt Formation + Show 4 more

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Abstract

A useful key intermediate for the dipeptidyl peptidase-4 (DPP-4) inhibitor, 3-aminopiperidine 1, was successfully resolved with an enantiomerically pure resolving agent, N-tosyl-(S)-phenylalanine 2, to give both stereoisomers (R)-1 and (S)-1 as a less-soluble diastereomeric salt with (S)-2, via a dielectrically controlled resolution (DCR) phenomenon.

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