Sodium Carbonate → trans-2-benzyl-3a-methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

Participants

Reaction Conditions

Reaction Steps

trans-2-Benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.561 mmol, 200 mg) was dissolved in DME (1 ml) and Ethanol (0.5 ml). 2 N sodium carbonate solution (1 ml) was added along with 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.842 mmol, 141 mg) and tetrakis(triphenylphosphine)Pd(0) (0.028 mmol, 32.4 mg). The reaction mixture was heated at 160° C. for 15 minutes in a microwave reactor and then diluted with water. The resulting mixture was extracted with DCM and the combined organic extracts were concentrated in vacuo to give a crude residue that was purified by silica column chromatography (eluting with 10% EtOAc in heptane) to afford trans-2-benzyl-3a-methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (134 mg), m/z: 318.2 [M+H]+.

Provenance & Evidence