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Synlett 2006(6): 889-892
DOI: 10.1055/s-2006-939036
DOI: 10.1055/s-2006-939036
LETTER
© Georg Thieme Verlag Stuttgart · New York
Practical Synthesis of (S)-Pyrrolidin-2-yl-1H-tetrazole, Incorporating Efficient Protecting Group Removal by Flow-Reactor Hydrogenolysis
Further Information
Publication History
Received
6 February 2006
Publication Date:
14 March 2006 (online)


Abstract
A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-CubeTM (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream)
Key words
tetrazole - asymmetric - synthesis - organocatalysis - flow - hydrogenation