M. J. D. Nie-Sarink, U. Pandit
1979
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0
Influential Citations
5
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
4-tert-Butylcyclohexanone undergoes reductive amination to a mixture of isomeric 1-pyrrolidino-4-tert-butylcyclohexanes (3a,b) upon reduction with Hantzsch ester (2), in the presence of pyrrolidine and the corresponding perchlorate. Under standardized conditions (10 equiv. of pyrrolidine, 1 equiv. of pyrrolidine perchlorate), only 75% of the product (3a,b) is formed via reduction by the Hantzsch ester. The remaining 25% is produced in a process which involves a hydride transfer from either the pyrrolidine (secondary amine) or the enamine system, generated as an intermediate in the reaction to the corresponding iminium salt. The stereochemistry of the Hantzsch ester reduction has been investigated by the use of 4,4-dideutero-Hantzsch ester (7).