Trifluoroacetic acid → 5-[2-(4-Chlorophenyl)ethyl]-2-(3,5-dichlorophenyl)tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

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Reaction Steps

To prepare the compound of formula (Im), wherein R11 is chloro and m is 2, TFA (32 μl, 0.41 mmol) was added to an ice-cooled mixture of 4-chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamine (1.5 g, 5.25 mmol) (Preparation 14) and N-(3,5-dichlorophenyl)succinimide (1 g, 4.13 mmol, prepared according to Fujinami et al., Agr. Biol. Chem. [1972], p. 318, incorporated herein by reference) in methylene chloride (10 mL). The reaction mixture was allowed to warm to RT over 3 h. The solution was washed with ammonium hydroxide. The organic layer was dried over MgSO4 and concentrated in vacuo to afford after chromatography over silica gel (CH2Cl2) the above-referenced compound as a white solid (1.56 g). Mp=115° C. 1H NMR (CDCl3): 7.40 (1H, br s), 7.15-7.35 (4H, m), 7.07 (2H, d, J=8.3 Hz), 3.4-3.5 (2H, m), 3.3-3.4 (2H, m), 2.55-2.8 (4H, m), 2.35-2.5 (2H, m).

Provenance & Evidence