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Synthesis 1999; 1999(3): 435-440
DOI: 10.1055/s-1999-3399
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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
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Publication Date:
31 December 1999 (online)

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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