Dimethyl Sulfoxide → 2-[(7S)-1-benzyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide (5b) (230 mg) dissolved in Toluene (25 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (22 mg) and the reaction mixture was stirred at 80° C. for 2 h, then cooled to RT. DMSO (0.1 mL) was added to the reaction and the mixture stirred for 1 h, then concentrated. The crude product was directly purified via flash chromatography (gradient—5%, 10%, 15% EtOAc/hexanes) to give a diastereomeric mixture (1.5:1) of the title compound. (168 mg, 78%).

Provenance & Evidence