Sodium borohydride → rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

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Reaction Steps

A solution of 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione (1.514 g; 3.69 mmol) in anh. EtOH (20 ml) was treated with NaBH4 (700 mg; 18.49 mmol), and the mixture was stirred at rt, under nitrogen, for 2 h. After concentration to dryness under reduced pressure, the resulting residue was treated with 1 M aq. HCl and with water. After extractions with DCM, the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one as a colorless foam. LC-MS (conditions A): tR=0.81 min.; [M+H]+: 412.27 g/mol.

Provenance & Evidence