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Synthesis of 5,5-Bis(hydroxymethyl)-N-hydroxypyrrolidin-2-one Derivatives

Mironiuk-Puchalska E., Kołaczkowska E., Sas W.

Polish Journal of Chemistry

2008

Vol. 82, nr 8

1553-1553

2,2-Disubstituted methyl 3-(5-ni tro-1,3-dioxane-5-yl)propanoate derivatives were reduced with aluminum amalgam in a THF/water mixture to afford the corresponding methyl 3-(5-hydroxylamino-1,3-dioxane-5-yl)propanoates in high yields. Acetican hydride acetylation of 3-(5-hydroxylamino-2,2-dimethyl-1,3-dioxane-5-yl)propanoate gave N-acetyl derivative in 91% yield. Heating of the gamma-(hydroxylamino)esters in to luene furnished the mixture from which the corresponding N-hydroxypyrrolidin-2-one derivatives were isolated in 38–56% yield. Unexpectedly, the cyclization appeared to be the critical step of synthesis of title pyrrolidin-2-ones.