Synlett 2010(5): 749-752  
DOI: 10.1055/s-0029-1219344
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Nitropyrrolidines via Dipolar Cycloaddition Reactions Using a Modular Flow Reactor

Marcus Baumann, Ian R. Baxendale, Steven V. Ley*Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)767798; e-Mail: svl1000@cam.ac.uk;
Further Information

Publication History

Received 20 November 2009
Publication Date:
25 January 2010 (eFirst)

Abstract

The generation and subsequent use of unstabilised azomethine ylides in dipolar cycloaddition reactions within a flow microreactor is demonstrated. The 3-nitropyrrolidines produced were furthermore subjected to chemoselective hydrogenation reactions using the H-Cube® system. To ensure product purities in excess of 90-95%, immobilised scavengers were successfully employed.