HCID 86651805, compound → (3S,5'S)-tert-butyl 5'-(4-chlorobenzoyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Participants

Reaction Steps

To a stirred solution of (3S,5′S)-tert-butyl 5′-(methoxy(methyl)carbamoyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (310 mg, 0.826 mmol) in THF (4 mL) was added 4-chloro phenylmagnesium bromide (1.0 N in THF, 2.89 mL, 2.89 mmol) at about 0° C. The reaction mixture was warmed to about room temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified by column chromatography (hexanes:EtOAc, 1:1) to give (3S,5′S)-tert-butyl 5′-(4-chlorobenzoyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.240 g, 68%). LCMS (APCI+) m/z 427, 429 [M+H]+; Rt=3.94 min.

Provenance & Evidence