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Synthesis of 2-dialkylaminomethyltetrahydrofuran-3-ols

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of esters of 4-R-3-methyl-2,3,4,5-diepoxyvaleric acids with secondary amines leads to the formation of esters of 4-R-5-dialkylamino-4-hydroxy-3-methyl-2,3-epoxyvaleric acids. The reduction of the latter with lithium tetrahydroaluminate and the cyclization of the reduction products in the presence of p-toluenesulfonic acid has given 2-dialkylaminoethyltetrahydrofuran-3-ols, the methiodides of which possess ganglion-blocking activity.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1446, November, 1973.

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Stanishevskii, L.S., Tishchenko, I.G., Tyvorskii, V.I. et al. Synthesis of 2-dialkylaminomethyltetrahydrofuran-3-ols. Chem Heterocycl Compd 9, 1303–1306 (1973). https://doi.org/10.1007/BF00470328

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  • DOI: https://doi.org/10.1007/BF00470328

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