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KMID : 1059519920360040598
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Journal of the Korean Chemical Society
1992 Volume.36 No. 4 p.598 ~ p.602
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A Study on the Synthesis of 2-Piperidylglycine
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Chung Kyoo-Hyun
Wang Kyu-Jeung
Lee Hyung-Gu
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Abstract
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2-Piperidylglycine will be a model compound for the synthesis of antitumor agent 593A. 2-Piperidylglycine may be synthesized by alkylation of glycine equivalent to C-2 position of piperidine ring. δ-Valerolactam was reacted with trimethyl oxonium tetrafluoroborate to give 2-methoxy-1-piperideine. The imino ether was not condensed with ethyl phthalimidoacetate, one of glycine equivalents, but with ethyl nitroacetate to afford ethyl nitro-2-piperidylene acetate. The subsequent hydrogenation over Pt/C gave ethyl 2-piperidyl glycinate. Because the Z-configuration of the condensed product was assigned by nmr, the stereochemistry of ethyl 2-piperidyl glycinate different from that of Agent 593A.
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