1,2-Dimethoxyethane → cis-2-benzyl-3a-methyl-6-vinyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

Participants

Reaction Conditions

Reaction Steps

cis-2-Benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.421 mmol, 150 mg) was dissolved in DME (1 ml) and ethanol (0.5 ml). 2 N sodium carbonate solution (1 ml), tetrakis(triphenylphosphine)Pd(0) (0.021 mmol, 24.32 mg) and 2,4,6-trivinyl-1,3,5,2,4,6-trioxatriborinane-pyridine complex (0.631 mmol, 152 mg) were added and the reaction mixture was heated at 160° C. for 15 minutes in a microwave reactor. The reaction mixture was diluted with water and extracted with DCM (3×). The combined organic extracts were concentrated in vacuo and then purified by silica column chromatography (eluting with 10% EtOAc in heptane) to afford cis-2-benzyl-3a-methyl-6-vinyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (100 mg), m/z: 304.2 [M+H]+.

Provenance & Evidence