[FTIR study on the reduction of 1-benzyl-3-hydroxypyrrolidine-2,5-dione]

Guang Pu Xue Yu Guang Pu Fen Xi. 2012 May;32(5):1238-40.
[Article in Chinese]

Abstract

The title compound was synthesized by reducing (S)-1-benzyl-3-hydroxypyrrolidine-2, 5-dione with sodium borohydride-iodin. The raw material, intermediate, and the end product were characterized by IR spectra and the mechanism of reduction of imide by sodium borohydride-iodin was also studied by IR spectra. According to the IR spectra, it was concluded that the product was (S)-1-bezyl-3-hydroxypyrrolidine. The mechanism of the reduction is that borane, formed in situ by reacting sodium borohydride with iodine, partly was conjugated to carbonyl to form four-member-ring intermediate and partly conjugated to nitrogen. (S)-1-benzyl-3-hydroxypyrrolidine/BH3 complex was gained when the reduction finished. The title compound was obtained by removing borane from the complex in methanol.

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