Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate

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.

doi:10.1021/jo400647t

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dc.contributor.author	Slattery, Catherine N.
dc.contributor.author	Deasy, Rebecca E.
dc.contributor.author	Maguire, Anita R.
dc.contributor.author	Kopach, Michael E.
dc.contributor.author	Singh, Utpal K.
dc.contributor.author	Argentine, Mark D.
dc.contributor.author	Trankle, William G.
dc.contributor.author	Scherer, Roger B.
dc.contributor.author	Moynihan, Humphrey A.
dc.date.accessioned	2016-08-17T08:54:20Z
dc.date.available	2016-08-17T08:54:20Z
dc.date.issued	2013-05-30
dc.identifier.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	en
dc.identifier.volume	78	en
dc.identifier.issued	12	en
dc.identifier.startpage	5955	en
dc.identifier.endpage	5963	en
dc.identifier.issn	0022-3263
dc.identifier.uri	http://hdl.handle.net/10468/2998
dc.identifier.doi	10.1021/jo400647t
dc.description.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.	en
dc.description.sponsorship	Enterprise Ireland (financial support of C.N.S. and R.E.D.)	en
dc.format.mimetype	application/pdf	en
dc.language.iso	en	en
dc.publisher	American Chemical Society	en
dc.rights	© 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	en
dc.subject	Efficient process	en
dc.subject	Formylation	en
dc.subject	Hydride reduction	en
dc.subject	Hydroxymethylation	en
dc.subject	Pharmaceutical intermediates	en
dc.subject	Scale-up	en
dc.subject	Synthetic approach	en
dc.subject	Hydroxymethyl groups	en
dc.title	Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate	en
dc.type	Article (peer-reviewed)	en
dc.internal.authorcontactother	Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie	en
dc.internal.availability	Full text available	en
dc.date.updated	2016-08-16T15:58:58Z
dc.description.version	Submitted Version	en
dc.internal.rssid	264353326
dc.contributor.funder	Enterprise Ireland	en
dc.description.status	Peer reviewed	en
dc.identifier.journaltitle	Journal of Organic Chemistry	en
dc.internal.copyrightchecked	Yes	en
dc.internal.licenseacceptance	Yes	en
dc.internal.IRISemailaddress	a.maguire@ucc.ie	en