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

Jevgenijs Kuznecovs, Vladislavs Baskevics, Natalja Orlova, Sergey Belyakov, Ilona Domračeva, Maksims Vorona, Grigory Veinberg
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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.


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.

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