Tetrahedron

A convenient synthesis of 1′-H-spiro-(indoline-3, 4′-piperidine) and its derivatives

JS Xie, CQ Huang, YY Fang, YF Zhu

Index: Xie, Jian-Shu; Huang, Charles Q.; Fang, Yan-Yan; Zhu, Yun-Fei Tetrahedron, 2004 , vol. 60, # 22 p. 4875 - 4878

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Citation Number: 11

Abstract

A simple synthetic route has been developed to prepare 1′-H-spiro (indoline-3, 4′- piperidine)(). Dialkylation of 2-fluorophenylacetonitrile with N-(tert-butyloxycarbonyl)-bis (2- chloroethyl) amine () gave. Deprotection of Boc followed by cyclization resulted in 67% overall yield. Selective Boc or Cbz protection of 1′-N gave or with 90 and 85% yield, respectively. Thus, in a five-step procedure, and were synthesized from commercially ...