Thermal Overman Rearrangement of a Glucal Derivative in a Tube Reactor on Pilot Plant Scale

Organic Process Research and Development

Volumn 20, Issue 2, 2016, Pages 446-451

  Amann, Franz ^a   Frank, Michael ^a   Rhodes, Robert ^b   Robinson, Andrew ^b   Kesselgruber, Martin ^c   Abele, Stefan ^c  

^a Carbogen Amcis AG   (Switzerland)

^b Carbogen Amcis Ltd   (United Kingdom)

^c ACTELION PHARMACEUTICALS LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

ACTIVE PHARMACEUTICAL INTERMEDIATES; BATCH MODES; CONTINUOUS PROCESS; FLOW CHEMISTRY; OVERMAN REARRANGEMENT; PILOT PLANT SCALE; TRICHLOROACETIMIDATE; TUBE REACTORS;

PILOT PLANTS;

EID: 84975780867     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/acs.oprd.5b00322     Document Type: Article

References (9)

1. Kriek, N. M. A. J.; van der Hout, E.; Kelly, P.; van Meijgaarden, K. E.; Geluk, A.; Ottenhoff, T. H. M.; van der Marel, G. A.; Overhand, M.; van Boom, J. H.; Valentijn, A. R. P. M.; Overkleeft, H. S. Eur. J. Org. Chem. 2003, 2003, 2418-2427 10.1002/ejoc.200200710
2. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901-2910 10.1021/ja00426a038
3. Overman, L. E. Acc. Chem. Res. 1980, 13, 218-224 10.1021/ar50151a005
4. Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225-12231 10.1021/ja027271p
5. Nishikawa, T.; Ohyabu, M. A. N.; Isobe, M. J. Org. Chem. 1998, 63, 188-192 10.1021/jo9713924
6. Using Continuous Processes to Increase Production: Anderson, N. G. Org. Process Res. Dev. 2012, 16, 852-869 10.1021/op200347k
7. Managing Hazardous Reactions and Compounds in Process Chemistry; Pesti, J. A.; Abdel-Magid, A. F., Eds.; Volume 1181, published (Web): November 20, 2014.
8. Abele, S.; Höck, S.; Schmidt, G.; Funel, J.-A.; Marti, R. Org. Process Res. Dev. 2012, 16, 1114-1120 10.1021/op200320w
9. Kilcher, E.; Freymond, S.; Vanoli, E.; Marti, R.; Schmidt, G.; Abele, S. Org. Process Res. Dev. 2015, 10.1021/acs.oprd.5b00046.