title: Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate.
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.
authors.affiliation: Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
authors.forename: Catherine N
authors.initials: CN
authors.lastname: Slattery
authors.forename: Rebecca E
authors.initials: RE
authors.lastname: Deasy
authors.forename: Anita R
authors.initials: AR
authors.lastname: Maguire
authors.forename: Michael E
authors.initials: ME
authors.lastname: Kopach
authors.forename: Utpal K
authors.initials: UK
authors.lastname: Singh
authors.forename: Mark D
authors.initials: MD
authors.lastname: Argentine
authors.forename: William G
authors.initials: WG
authors.lastname: Trankle
authors.forename: Roger Brian
authors.initials: RB
authors.lastname: Scherer
authors.forename: Humphrey
authors.initials: H
authors.lastname: Moynihan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis*; D000928:Antidepressive Agents / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000928:Antidepressive Agents; D009025:Morpholines; C568831:alpha-((5-fluoro-2-methoxyphenyl)methyl)-alpha-(tetrahydro-2H-pyran-4-yl)-2-morpholinemethanol; D010626:Phenylethyl Alcohol