A Short and Efficient Synthesis of 3-[2,2,2-Trifluoroethyl]hexahydro-2H-1,4-diazepin-2-one

Jaume Balsells; Marjorie Waters; Karl Hansen; Gerard R. Kieczykowski; Zhiguo J. Song

doi:10.1055/s-2007-983876

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2007(18): 2779-2781
DOI: 10.1055/s-2007-983876

SHORTPAPER

A Short and Efficient Synthesis of 3-[2,2,2-Trifluoroethyl]hexahydro-2H-1,4-diazepin-2-one

Jaume Balsells*, Marjorie Waters, Karl Hansen, Gerard R. Kieczykowski, Zhiguo J. Song
Department of Process Research and Medicinal Chemistry Department, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065, USA
Fax: +1(732)5941499; e-Mail: Jaume_Balsells@merck.com;

Further Information

Publication History

Received 16 February 2007
Publication Date:
29 August 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A short, high yielding, five-step synthesis of the pharmaceutically interesting fluorinated heterocycle, 3-[2,2,2-trifluoroethyl]hexahydro-2H-1,4-diazepin-2-one, has been developed.

Key words

lactam - fluorine - alkylation - Michael addition - hydrogenation

References

1a Biftu T, Liang G.-B, Qian X, Weber AE, and Feng DD. inventors; PCT Int. Appl. WO 2004037169. ; Chem. Abstr. 2004, 140, 391494
1b Biftu T, Feng DD, Liang G.-B, and Qian X. inventors; PCT Int. Appl. WO 2004103276. ; Chem. Abstr. 2005, 142, 23098
1c Biftu T, Feng DD, Gao Y.-D, Singh S, and Weber AE. inventors; PCT Int. Appl. WO 2006009886. ; Chem. Abstr. 2006, 144, 171018
1d Biftu T, Song ZJ, Zhang F, Rosner T, Hansen K, and Armstrong JD. inventors; PCT Int. Appl. WO 2006065826. ; Chem. Abstr. 2006, 145, 63148
2a Han Y. Mierke DF. Chorev M. Biopolymers 2002, 64: 1

Crossref Google Scholar
2b Breslin HJ. Kukla MJ. Kromis T. Cullis H. De Knaep F. Pauwels R. Andries K. De Clerq E. Janssen MAC. Paul AJ. Bioorg. Med. Chem. 1999, 7: 2427

Crossref Google Scholar
2c Weitz IS. Pellegrini M. Mierke DF. Chorev M. J. Org. Chem. 1997, 62: 2527

Crossref Google Scholar
3a Nakajima N. Isobe T. Irisa S. Ubukata M. Heterocycles 2003, 59: 107

Crossref Google Scholar
3b Knapp S. Moriello GJ. Nandan SR. Emge TJ. Doss GA. Mosley RT. Chen L. J. Org. Chem. 2001, 66: 5822

Crossref Google Scholar
4 Chassonery D. Chastrette F. Chastrette M. Blanc A. Mattioda G. Bull. Soc. Chim. Fr. 1994, 131: 188

Google Scholar
5 Pohlmann A. Guillaume D. Quirion J.-C. Husson H.-P. Tetrahedron Lett. 1997, 38: 5809

Crossref Google Scholar
6 Auty JMA. Churcher I. Hayes CJ. Synlett 2004, 1443

Article in Thieme Connect Google Scholar
7a Walborsky HM. Baum ME. J. Org. Chem. 1956, 21: 538

Article in Thieme Connect Google Scholar
7b Steglich W. Heininger HU. Dworschak H. Weygand F. Angew. Chem., Int. Ed. Engl. 1967, 6: 807

Article in Thieme Connect Google Scholar
7c Maki Y. Inukai K. Yuki Gosei Kagaku Kyokaishi 1976, 34: 722 ; Chem. Abstr. 1977, 87, 68600

Article in Thieme Connect Google Scholar
7d Tsushima T. Kawada K. Shoichi I. Uchida N. Shiratori O. Higaki J. Hirata M. Tetrahedron 1988, 44: 5375

Article in Thieme Connect Google Scholar
7e Schedel H. Dmowski W. Burger K. Synthesis 2000, 1681

Article in Thieme Connect Google Scholar
8a O’Donnell MJ. Boniece JM. Earp SE. Tetrahedron Lett. 1978, 19: 2641

Crossref Google Scholar
8b Stork G. Leong AYW. Touzin AM. J. Org. Chem. 1976, 41: 3491

Crossref Google Scholar
8c O’Donnell MJ. Acc. Chem. Res. 2004, 37: 506

Crossref Google Scholar