3-Chloro-2-fluorobenzaldehyde → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-one prepared in Example 3 (1.2 g, 4.3 mmol) in pyridine (50 mL) was added 3-chloro-2-fluoro-benzaldehyde (Oakwood) (0.68 g, 4.3 mmol). The reaction mixture was heated at 100° C. for 2 h. The mixture was cooled to room temperature and concentrated. The residue was dissolved into ethyl acetate, washed with aqueous saturated CuSO4 solution, and brine. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (50-100% EtOAc in hexanes) to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3′-pyrrolidin]-2-one as a white solid (Yield, 0.29 g, 16%).

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