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Synfacts 2010(11): 1312-1312  
DOI: 10.1055/s-0030-1258762
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of N-Substituted Pyrrolidinone Derivatives via the Ugi Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
Z. Liu, A. Nefzi*
Torrey Pines Institute for Molecular Studies, Port Saint Lucie, USA
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Publikationsdatum:
21. Oktober 2010 (online)

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Significance

The polymer-supported Ugi reaction of 2 was carried out with N-Boc-4-piperidin­one and benzyl isocyanide to give the Ugi product 3. Removal of the Boc group followed by the coupling with sulfonyl chlorides, isocyanates, isothiocyanates or carboxylic acids afforded 5. The resin support of 5 was cleaved with HF to afford the corresponding amides 6 in 68-85% yield (9 examples).