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Paper | Special issue | Vol 77, No. 1, 2009, pp.255-261
Published online, 11th April, 2008
DOI: 10.3987/COM-08-S(F)1
One-Pot Synthesis of 3,3-Dimethylpyrrolidine-2-carbonitriles from 4-Chloro-2,2-dimethylbutanal in Water

Matthias D’hooghe, Berten Van Driessche, and Norbert De Kimpe*

*Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium


Treatment of 4-chloro-2,2-dimethylbutanal, prepared in high yield by means of a three-step procedure starting from ethyl isobutyrate, with successively sodium bisulphite, a primary amine and potassium cyanide in water afforded novel 1-alkyl- and 1-aryl-3,3-dimethylpyrrolidin-2-carbonitriles in a convenient and environmentally benign way.