Facile Non-Racemizing Route for the N-Alkylation of Hindered Secondary Amines

Shabana S. Insaf; Donald T. Witiak

doi:10.1055/s-1999-3399

Synthesis 1999; 1999(3): 435-440
DOI: 10.1055/s-1999-3399

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Facile Non-Racemizing Route for the N-Alkylation of Hindered Secondary Amines

Shabana S. Insaf^* , Donald T. Witiak

^*Division of Medicinal Chemistry, School of Pharmacy, University of Wisconsin at Madison, Madison, Wisconsin 53706, USA; Fax +1(7 81)7 68-00 40; E-mail: sinsat@scriptgen.com

Abstract

PDF Download All articles of this category

A simple, generally high yielding, method for the N-alkylation of sterically hindered secondary amines bearing α-substituents is described. Alkyl tosylates in the presence of 1,2,2,6,6-pentamethylpiperidine and toluene are essential for the production of the respective tertiary amines. Chiral amino acid derivatives studied do not racemize under the reaction conditions.

N-alkylation - secondary amines - substitution - tosylate - hindered nucleophiles

PDF (159 kb)