Skip to main content
Log in

Triton-B Catalyzed, Efficient, One-Pot Synthesis of Carbamate Esters from Alcoholic Tosylates

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

A novel process for the one-step chemoselective conversion of a variety of alcoholic tosylates into carbamates serving as protected amines was developed using benzyltrimethylammonium hydroxide (Triton-B) in the presence of gaseous carbon dioxide. Thus carbamate esters of different amines were prepared in very good to excellent yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • a) Adams P, Baron FA (1965) Chem Rev 65: 567

  • a) Ray S, Chaturvedi D (2004) Drugs of the Future 29: 343; b) Ray S, Pathak SR, Chaturvedi D (2005) Drugs of the Future 30: 161

    Google Scholar 

  • a) Mateen A, Chapalamadugu S, Kashar B, Bathi AR, Chaudhary GR (1994) Biol Degrad Biorem Toxic Chem 198; b) Wigfield YY (1996) Food Sci Technol (NY) 77: 1501

  • a) Snieckus V (1990) Chem Rev 90: 879; b) Cleraland WW, Andrews TS, Gutteridge S, Hartman FC, Lorimer GH (1998) Chem Rev 98: 549; c) Tanaka F (2002) Chem Rev 102: 4885

  • TW Greene PGM Wuts (1999) Protecting Groups in Organic Synthesis 3rd ed. John Wiley and Sons Inc; New York 503

    Google Scholar 

  • a) Mayer JP, Lewis GS, Curtius MJ, Zhang J (1997) Tetrahedron Lett 38: 8445; b) Buchstaller HP (1998) Tetrahedron 54: 3465; c) Holte PT, Thijs L, Zwanenburg B (1998) Tetrahedron Lett 39: 7404

  • a) Matsui T, Kondo T, Nishita Y, Itadani S, Tsuruta H, Fujita S, Omawari N, Sakai M, Nakazawa S, Ogata A, Mori H, Ohno H, Obata T, Nakai H, Toda M (2002) Bioorg Med Chem Lett 12: 907; b) Seko T, Kato M, Kohno H, Ono S, Hashimura K, Takimizu H, Nakai K, Maegawa H, Katsube N, Toda M (2002) Bioorg Med Chem Lett 12: 915

    Google Scholar 

  • DPN Satchell RS Satchell (1975) Chem Soc Rev 4 231 Occurrence Handle10.1039/cs9750400231 Occurrence Handle1:CAS:528:DyaE2MXkvFGktr0%3D

    Article  CAS  Google Scholar 

  • S Raucher DS Jones (1985) Synth Commun 15 1025 Occurrence Handle1:CAS:528:DyaL28XitVKgsro%3D

    CAS  Google Scholar 

  • a) Leung TW, Domblk BD (1992) Chem Commun 3: 205; b) Mizuno T, Takahashi J, Ogawa A (2002) Tetrahedron 58: 7805

  • a) Casedei MA, Inesi A, Moracci FM, Rossi L (1996) Chem Commun 2575; b) Casadei MA, Moracci FM, Zappia G, Inesi A, Rossi L (1997) J Org Chem 62: 6754; c) Feroci M, Inesi A, Rossi L (2000) Tetrahedron Lett 41: 963

  • MA Yoshida N Hara S Okuyama (2000) Chem Commun 2 151

    Google Scholar 

  • R Mahe Y Sasaki C Bruneau PH Dixneuf (1989) J Org Chem 54 1518 Occurrence Handle10.1021/jo00268a008 Occurrence Handle1:CAS:528:DyaL1MXhsFektrw%3D

    Article  CAS  Google Scholar 

  • a) Chaturvedi D, Kumar A, Ray S (2002) Synth Commun 32: 2651; b) Chaturvedi D, Kumar A, Ray S (2003) Tetrahedron Lett 44: 7637; c) Chaturvedi D, Ray S (2006) Monatsh Chem 137: 201

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 311 Occurrence Handle1:CAS:528:DC%2BD28XitVCit70%3D

    CAS  Google Scholar 

  • GW Kabalka M Varma RS Varma PC Srivasava FF Knapp (1986) J Org Chem 51 2386 Occurrence Handle10.1021/jo00362a044 Occurrence Handle1:CAS:528:DyaL28XktVKht7c%3D

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Devdutt Chaturvedi.

Additional information

Present address: Institute of Organic and Biomolecular Chemistry, Georg-August University, D-37077, Göttingen, Germany

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chaturvedi, D., Ray, S. Triton-B Catalyzed, Efficient, One-Pot Synthesis of Carbamate Esters from Alcoholic Tosylates. Monatsh. Chem. 137, 459–463 (2006). https://doi.org/10.1007/s00706-005-0452-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-005-0452-2

Navigation