Abstract
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. ${\delta}$-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.
2-Piperidylglycine은 항종양제 593A의 합성을 위한 모델이 될 수 있다. 2-Piperidylglycine은 piperidine의 C-2 위치에 glycine 동등체를 도입하여 합성할 수 있다. ${\delta}$-Valerolactam에 trimethyl oxonium tetrafluoroborate를 가하여 2-methoxy-1-piperideine을 합성하였다. 이 imino ether는 glycine 동등체인 ethyl phthalimidoacetate와 반응하지 않았으나 ethyl nitroacetate와는 축합하여 ethyl nitro-2-piperidylene acetate를 주었다. 이를 Pt/C 촉매하의 수소첨가로 ethyl 2-piperidyl glycinate을 얻을 수 있었는데 축합물인 ethyl nitro-2-piperidylene의 이중결합이 Z-configuration을 가져 ethyl 2-piperidyl glycinate는 항종양제 593A와 다른 입체화학을 가지게 된다.
