Dimethyl Sulfoxide → tert-Butyl 3-(2'-cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-yloxy)-4-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of methyl 2′-cyano-5-hydroxy-4′-methylbiphenyl-3-carboxylate (300 mg, 1.1 mol), potassium carbonate (320 mg, 2.4 mmol), DMSO (8 mL), and tert-butyl 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylate (2.4 mmol) (J. Am. Chem. Soc. 2008, 130, 3900) was heated at 135° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-50% EtOAc/hexane) to afford the title compound.

Provenance & Evidence