An application of borane as a protecting group for pyridine.
Efforts to couple 4 with 12 employing base mediation are problematic due to the formation of 6. To circumvent this issue, 12 was converted to the pyridine borane complex (13). Alkylation of 4 with 13 provided 3 after removal of the borane under acidic conditions and saponification of the ester.
Zajac
Matthew A
MA
GlaxoSmithKline, Synthetic Chemistry 709 Swedeland Road, P.O. Box 1539, King of Prussia, Pennsylvania 19406, USA. matthew.a.zajac@gsk.com
D000478:Alkylation; D001880:Boranes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D011725:Pyridines / Q000737:chemistry*
D001880:Boranes; D001896:Boron Compounds; D004952:Esters; D011725:Pyridines; C041928:pyridine borane; C023666:pyridine