252002-43-0Relevant articles and documents
A convenient synthesis of 1′-H-spiro-(indoline-3,4′-piperidine) and its derivatives
Xie, Jian-Shu,Huang, Charles Q.,Fang, Yan-Yan,Zhu, Yun-Fei
, p. 4875 - 4878 (2007/10/03)
A simple synthetic route has been developed to prepare 1′-H- spiro(indoline-3,4′-piperidine) (1d). Dialkylation of 2- fluorophenylacetonitrile with N-(tert-butyloxycarbonyl)-bis(2-chloroethyl)amine (5) gave 6. Deprotection of Boc followed by cyclization resulted 1d in 67% overall yield. Selective Boc or Cbz protection of 1′-N gave 1a or 1b with 90 and 85% yield, respectively. Thus, in a five-step procedure, 1a and 1b were synthesized from commercially available reagents in over 50% overall yield. All 3 compounds (1a, 1b and 1d) can be utilized as templates to synthesize compounds for GPCR targets.