Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate
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Date
2013-05-30
Authors
Slattery, Catherine N.
Deasy, Rebecca E.
Maguire, Anita R.
Kopach, Michael E.
Singh, Utpal K.
Argentine, Mark D.
Trankle, William G.
Scherer, Roger B.
Moynihan, Humphrey A.
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Published Version
Abstract
An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.
Description
Keywords
Efficient process , Formylation , Hydride reduction , Hydroxymethylation , Pharmaceutical intermediates , Scale-up , Synthetic approach , Hydroxymethyl groups
Citation
Slattery, C. N., Deasy, R. E., Maguire, A. R., Kopach, M. E., Singh, U. K., Argentine, M. D., Trankle, W. G., Scherer, R. B. and Moynihan, H. A. (2013) 'Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate', Journal of Organic Chemistry, 78(12), pp. 5955-5963. http://dx.doi.org/10.1021/jo400647t
Copyright
© 2013 American Chemical Society. This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo400647t