Catalyst-Free Chemoselective N-tert-Butyloxycarbonylation of Amines in Water

Sunay V. Chankeshwara and Asit K. Chakraborti*;
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India
Org. Lett., 2006, 8 (15), pp 3259–3262
DOI: 10.1021/ol0611191
Publication Date (Web): June 20, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, akchakraborti@niper.ac.in, ; , akchakraborti@rediffmail.com

Abstract

Abstract Image

Catalyst-free N-tert-butyloxycarbonylation of amines in water is reported. The N-t-Boc derivatives were formed chemoselectively without any isocyanate, urea, N,N-di-t-Boc, and O/S-t-Boc as side products. Chiral amines, esters of α-amino acids, and β-amino alcohol afforded optically pure N-t-Boc derivatives. Amino alcohol and 2-aminophenol afforded the N-t-Boc derivative without oxazolidinone formation. Selectivity was observed during competition of aromatic amine vs aliphatic amine, amine vs amino acid ester, amine vs amino alcohol, and primary amine vs secondary amine.

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History

  • Published In Issue July 20, 2006
  • Received May 7, 2006

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