Dielectrically controlled resolution (DCR) of 3-aminopiperidine via diastereomeric salt formation with N-tosyl-(S)-phenylalanine |
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| Authors: | Rumiko Sakurai Kenichi Sakai Koichi Kodama Masanori Yamaura |
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| Affiliation: | 1. Faculty of Pharmacy, Iwaki Meisei University, Iwaki, Fukushima 970-8551, Japan;2. Technology Development Division, Toray Fine Chemicals Co., Ltd, Nagoya, Aichi 455-8502, Japan;3. Department of Applied Chemistry, Saitama University, Sakura-ku, Saitama 338-8570, Japan |
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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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