Simple Preparation of O-Substituted Hydroxylamines from Alcohols

Sébastien Albrecht; Albert Defoin; Céline Tarnus

doi:10.1055/s-2006-926440

PAPER

Simple Preparation of O-Substituted Hydroxylamines from Alcohols

Sébastien Albrecht, Albert Defoin*, Céline Tarnus
Laboratoire de Chimie Organique et Bioorganique, UMR 7015, École Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3 rue Alfred Werner, 68093 Mulhouse Cédex, France
Fax: +33(3)89336875 ; e-Mail: A.Defoin@uha.fr;

Abstract

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Abstract

A direct preparation of O-substituted hydroxylamines from alcohols is described by O-alkylation of tert-butyl N-hydroxycarbamate with the methanesulfonates of respective alcohols, followed by acidic N-deprotection.

Key words

amination - nucleophilic substitution - hydroxylamine

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References

1 Adamczyk M. Reddy RE. Synth. Commun. 2001, 41: 579

2 Kim D.-K. Gam J.-S. Kim Y.-W. Lim J.-S. Kim H.-T. Kim KH. J. Med. Chem. 1997, 40: 2363

3a Nicolaus BJR. Pagani G. Testa E. Helv. Chim. Acta 1962, 45: 1381

3b Nicolaus BJR. Pagani G. Testa E. Helv. Chim. Acta 1962, 45: 1393

3c See also: Zeeh B. Metzger H. Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie Müller E. Thieme Verlag; Stuttgart: 1971. Vol. X-1: p.1184 ff

4 Zeeh B. Metzger H. Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie Müller E. Thieme Verlag; Stuttgart: 1971. Vol. X-1: p.1183 ff

5 Zeeh B., Metzger H.; Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie; Müller E., Thieme Verlag: Stuttgart, 1971; Vol. X-1, 1192 ff

6 Grochowski E. Jurczak J. Synthesis 1976, 682

7 Jones DS. Hammaker JR. Tedder ME. Tetrahedron Lett. 2000, 41: 1531

8 Gabriel S. Ber Dtsch. Chem. Ges. 1887, 20: 2224

9 Ing HR. Manske RHF. J. Chem. Soc. 1926, 2348

10 Foot OF. Knight DW. Chem. Commun. 2000, 975

11 Theilacker W. Ebke K. Angew. Chem. 1956, 68: 303

12 Hight A. Prior T. Bell RA. Rangachari PK. J. Pharmacol. Exp. Ther. 1999, 288: 490

13 Behr JB. Chevrier C. Defoin A. Tarnus C. Streith J. Tetrahedron 2003, 59: 543

14 Burns DH. Miller JD. Chan H.-K. Delaney MO. J. Am. Chem. Soc. 1997, 119: 2125

15 Bly RS. Mateer RA. Tse K.-K. Veazey RL. J. Org. Chem. 1973, 38: 1518

16 Dennison PhR. Gibson A. Gray AIG. Patrick L. J. Chem. Soc., Perkin Trans. 1 1997, 721

17 Choudary BM. Chowdari NS. Naidu S. Kantam ML. Tetrahedron 2000, 56: 7291

18 Fischli A. Müller PM. Helv. Chim. Acta 1980, 63: 1619

19 Schumann EL. Heinzelman RV. Greig ME. Veldkamp W. J. Med. Chem. 1964, 7: 329

20 Macchia M. Menchini E. Nencetti S. Orlandini E. Rosello A. Belfiore MSt. Il Farmaco 1996, 51: 255

21 Mavunkel BJ. Rzeszotarski WJP. Kaplita V. DeHaven-Hudkins DL. Eur. J. Med. Chem. 1994, 29: 659

22 Choong I. Ellman JA. J. Org. Chem. 1999, 64: 6528

23 Ishikawa T. Kamiyama K. Matsunaga M. Tawada H. Iizawa Y. Okonogi K. Miyake A. J. Antibiot. 2000, 53: 1071