Novel methods for the synthesis of 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]- acetamide ((R)-phenotropil)

M. Vorona, G. Veinberg, S. Vikainis, E. Kuznetsov, A. Lebedev, Yu Ponomarev, A. Chernobrovijs, L. Zvejniece, M. Dambrova

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Two novel methods have been developed for the preparation of 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide ((R)-Phenotropil). In the first, n-butyl (3R)-4-amino-3-phenylbutyrate is alkylated with haloacetamide in DMF in the presence of potassium phosphate monohydrate, and the intermediate 4-carbamoylmethylamino-3-phenylbutyrate is subsequently cyclized by refluxing in toluene in the presence of potassium phosphate monohydrate and tetrabutylammonium bromide. In the second, chloroacetonitrile is used under similar conditions in place of the haloacetamide. Both methods lead to (R)-Phenotropil in 40-60% yields calculated on the starting n-butyl (3R)-4-amino-3-phenylbutyrate.

Original languageEnglish
Pages (from-to)720-723
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume48
Issue number5
DOIs
Publication statusPublished - Aug 2012
Externally publishedYes

Keywords

  • 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl] acetamide
  • Alkylation
  • Cyclization
  • N-butyl (3R)-4-carbamoylmethylamino-3-phenylbutyrate
  • N-butyl (3R)-4-cyanomethyl-amino-3-phenylbutyrate

Field of Science

  • 1.4 Chemical sciences

Publication Type

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

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