反应详情

温度

190 °C

(E)-N-Benzyl-3-chloro-N-(2-methylbut-2-enyl)-1,2-dihydrocyclobutabenzene-1-carboxamide (0.971 mmol, 330 mg) was dissolved in bromobenzene (6 ml) and heated in a microwave reactor at 190° C. for 1 hour. The solvent was removed in vacuo and the resulting residue was purified by silica column chromatography (eluting with heptane then 5-20% ethyl acetate in heptane) to give (3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (229 mg) 1H NMR (400 MHz, CDCl3) ppm 7.42 (1H, d, ArH), 7.33-7.22 (7H, m, ArH), 4.57 (1H, d, CHHPh), 4.34 (1H, d, CHHPh), 3.34 (1H, s, CH), 3.24 (1H, d, CH), 3.01 (1H, d, CH), 2.90 (1H, dd, CH), 2.38 (1H, dd, CH), 1.77 (1H, m, CH), 1.04 (3H, s, CH3), 0.91 (3H, d, CH3) and (3aR*,4S*,9bS*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-H-benzo[e]isoindol-1-one (96 mg) 1H NMR (400 MHz, CDCl3) ppm 8.36 (1H, d, ArH), 7.45-7.13 (7H, m, 7×ArH), 4.55 (1H, d, CHHPh), 4.47 (1H, d, CHHPh), 3.40 (1H, s, CH), 3.07-2.94 (3H, m, 3×CH), 2.40 (1H, dd, CH), 2.21-2.10 (1H, m, CH2), 0.99 (3H, d, CH3), 0.68 (3H, s, CH3).

1. customThe solvent was removed in vacuo
2. customthe resulting residue was purified by silica column chromatography (
3. washeluting with heptane