| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344315 | Tetrahedron: Asymmetry | 2012 | 4 Pages |
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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(R)-3-Ammoniopiperidium bis((S)-N-tosyl-2-amino-3-phenylpropanoate) monohydrateC37H48N4O9S2[α]D25=-4.6 (c 0.01, MeOH/H2O = 1/1)Source of chirality: resolutionAbsolute configuration: (R,S)
(S)-3-Ammoniopiperidium bis((S)-N-tosyl-2-amino-3-phenylpropanoate)C37H46N4O8S2[α]D25=-7.0 (c 0.01, MeOH/H2O = 1/1)Source of chirality: resolutionAbsolute configuration: (S,S)
