Imidazole → (S)-tert-butyl 4-(3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-butyl 4-(3-(4-(2-acetylhydrazinecarbonyl)-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (960 mg, 2.01 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. under nitrogen. 1H-imidazole (341 mg, 5.02 mmol), triphenylphosphine (1158 mg, 4.41 mmol) and perbromomethane (1464 mg, 4.41 mmol) were added and the reaction was allowed to warm to ambient temperature overnight. The reaction was partitioned between water and EtOAc, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (100% EtOAc) to afford (S)-tert-butyl 4-(3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (680 mg, 1.48 mmol, 73.6% yield).

Provenance & Evidence