Novel and Efficient Debenzylation of N-Benzyltetrazole Derivatives with the Rosenmund Catalyst

Masahiko Seki

doi:10.1055/s-0034-1378585

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(23): 3249-3255
DOI: 10.1055/s-0034-1378585

paper

Novel and Efficient Debenzylation of N-Benzyltetrazole Derivatives with the Rosenmund Catalyst

Masahiko Seki*

Process R&D Department, Healthcare Business Division II, API Corporation, 2-3-4, Nihonbashi, Chuo-ku, Tokyo 103-0027, Japan Fax: +81(3)52050642 eMail: seki.masahiko@mm.api-corp.co.jp

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The Rosenmund catalyst (Pd/BaSO₄) was found to efficiently catalyze debenzylation of N-benzyltetrazole derivatives with ammonium formate by catalytic transfer hydrogenation under mild conditions. The protocol has been applied to functionalized substrates to provide various angiotensin II receptor blockers in excellent yields.

Key words

palladium - cleavage - hydrogen transfer - heterocycles - protecting groups

Volltext

Referenzen

References

1a Anderson NG. Practical Process Research & Development . Academic Press; Oxford: 2000
1b Green Chemistry in the Pharmaceutical Industry . Dunn P, Wells A, Williams MT. Wiley-VCH; Weinheim: 2010
1c The Art of Process Chemistry . Yasuda N. Wiley-VCH; Weinheim: 2011

For the importance of deprotection in the synthesis of carbapenems, see:

1d Seki M, Kondo K, Kuroda T, Yamanaka T, Iwasaki T. Synlett 1995; 609

2a Seki M. WO 2011061996, 2010
2b Seki M. ACS Catal. 2011; 1: 607
2c Seki M, Nagahama M. J. Org. Chem. 2011; 76: 10198
2d Seki M. Synthesis 2012; 44: 3231
2e Seki M. J. Synth. Org. Chem., Jpn. 2012; 70: 1295
2f Kocienski P. Synfacts 2013; 9: 6
2g Seki M In Science of Synthesis: Catalytic Transformations via C–H Activation. Yu J.-Q. Thieme; Stuttgart: in press
2h Seki M. WO 2014034868, 2014

3 Seki M. WO 2014051008, 2014
4 Graul A, Leeson P, Castaner J. Drugs Future 1997; 22: 1205
5 For a mechanism of Pd/BaSO₄-catalyzed hydrogenation, see: McEwen AB, Guttieri MJ, Maier WF, Laine RM, Shvo Y. J. Org. Chem. 1983; 48: 4436

For example, see:

6a Carini DJ, Duncia JV, Aldrich PE, Chiu AT, Johnson AL, Pierce ME, Price WA, Santella III JB, Wells GJ, Wexler RR, Wong PC, Yoo S.-E, Timmermans PB. M. W. M. J. Med. Chem. 1991; 34: 2525
6b Bernhart CA, Perreaut PM, Ferrari BP, Muneaux YA, Assens J.-LA, Clément J, Haudricourt F, Muneaux CF, Taillades JE, Vignal M.-A, Gougat J, Guiraudou PR, Lacour CA, Roccon A, Cazaubon CF, Brelière J.-C, Le Fur G, Nisato D. J. Med. Chem. 1993; 36: 3371
6c Kubo K, Kohara Y, Yoshimura Y, Inada Y, Shibouta Y, Furukawa Y, Kato T, Nishikawa K, Naka T. J. Med. Chem. 1993; 36: 2343
6d Wexler RR, Greenlee WJ, Irvin JD, Goldberg MR, Prendergast K, Smith RD, Timmermans PB. M. W. M. J. Med. Chem. 1996; 39: 625
6e Kurup A, Garg R, Carini DJ, Hansch C. Chem. Rev. 2001; 101: 2727

Zusatzmaterial

Supporting Information