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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St, Riga, LV-1006, Latvia

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

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  1. Jevgenijs Kuznecovs
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  2. Vladislavs Baskevics
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  3. Natalja Orlova
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  4. Sergey Belyakov
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  5. Ilona Domračeva
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  6. Maksims Vorona
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  7. Grigory Veinberg
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Corresponding authors

Correspondence to Jevgenijs Kuznecovs or Grigory Veinberg.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1297–1301

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Kuznecovs, J., Baskevics, V., Orlova, N. et al. Synthesis of a Fluorinated Derivative of Sigma-1 Receptor Modulator E1R: 2-[5-oxo-3-phenyl-2-(trifluoromethyl)pyrrolidin-1-yl]Acetamide. Chem Heterocycl Comp 56, 1297–1301 (2020). https://doi.org/10.1007/s10593-020-02814-1

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  • DOI: https://doi.org/10.1007/s10593-020-02814-1

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