N,N'-Dimethylethylenediamine → HCID 58305406, compound

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.05 mmol, 5.0 mol %), racemic (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (270 mg, 1.0 mmol), and K2CO3 (276 mg, 2.0 mmol), evacuated, and backfilled with argon. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), ethyl 3-iodobenzoate (278.8 mg, 1.01 mmol), and acetonitrile (1.5 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 23 hours. HPLC monitored the reaction finished. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether) to give the title compound as a yellow powder (290 mg, 72%). LC/MS m/e calcd. for C24H18ClNO3: 403, observed (M+H)+: 404.1.

Provenance & Evidence