Water → HCID 69082672, compound

Participants

Reaction Steps

A cooled (−78° C.) solution of rac-(3R*,5S*)-5-(2-fluoro-6-methoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one (compound corresponding to example 293; 355 mg; 0.88 mmol) in anh. DCM (8 ml) was treated dropwise with a solution of boron tribromide BBr3 (1.0 M in DCM; 4.45 ml; 4.45 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Water was added dropwise to the cooled (0° C.) reaction mixture, and the separated aq. layer was extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered and concentrated to dryness under reduced pressure affording rac-(3R*,5S*)-5-(2-fluoro-6-hydroxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one. LC-MS (conditions A): tR=0.83 min.; [M+H]+: 386.05 g/mol.

Provenance & Evidence