A scalable, enantioselective synthesis of the r2-adrenergic agonist, lofexidine

Ashish P. Vartak, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A scalable and high-yielding synthetic route toward pure enantiomers of the α2-adrenergic agonist, lofexidine hydrochloride, is presented. Salient features include a rapid one-pot amide alkylation-imidazoline formation sequence on the carboxamide function of α-(2,6-dichlorophenoxy) propionamide, while preserving the sensitive configuration about the α-carbon of the resulting product. A means to accelerate the sluggish O-alkylation of the carboxamide function of α-(2,6-dichlorophenoxy) propionamide by Me3O+BF4- is also described, which may be of general applicability.

Original languageEnglish (US)
Pages (from-to)415-419
Number of pages5
JournalOrganic Process Research and Development
Volume13
Issue number3
DOIs
StatePublished - May 15 2009

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