SYNTHESIS OF A FLUORINATED DERIVATIVE OF SIGMA-1 RECEPTOR MODULATOR E1R: 2-[5-OXO-3-PHENYL-2-(TRIFLUOROMETHYL)PYRROLIDIN-1-YL]ACETAMIDE

Authors

  • Jevgenijs Kuznecovs Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Vladislavs Baskevics Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Natalja Orlova Latvian Institute of Organic Synthesis;21 Aizkraukles str.; Riga LV 1006; Latvia
  • Sergey Belyakov Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Ilona Domračeva Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Maksims Vorona Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Grigory Veinberg Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

DOI:

https://doi.org/10.1007/5512

Keywords:

3-hydroxy-4-phenyl-5-(trifluoromethyl)-3-pyrrolin-2-one, 3-methylidene-4-phenyl-5-(trifluoromethyl)pyrrolidin-2-one, 2-[5-oxo- 3-phenyl-2-(trifluoromethyl)pyrrolidin-1-yl]acetamide, fluorination, ozonation.

Abstract

The ozonation of N-Boc-protected 3-methylidene-4-phenyl-5-(trifluoromethyl)pyrrolidin-2-one resulted in its transformation into 3-hydroxy-4-phenyl-5-(trifluoromethyl)-3-pyrrolin-2-one. Catalytic hydrogenation of its O-Boc-protected derivative introduced a way to reduce the double bond in combination with elimination of the hydroxy group leading to the formation of 4-phenyl-5-(trifluoromethyl)pyrrolidin-2-one as an intermediate in the synthesis of fluorinated E1R structural derivative 2-[5-oxo-3-phenyl-2-(trifluoromethyl)pyrrolidin-1-yl]acetamide.

Downloads

Published

2020-11-05

Issue

Vol. 56 No. 10 (2020)

Section

Original Papers