To a solution of 6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-1H-benzo[g]quinolin-2-one (130 mg, 0.50 mmol) in THF (4 mL) was added NaH (18 mg, 0.76 mmol) in one portion at ambient temperature. To this solution was added methyl 4-(bromomethyl)-benzoate (229 mg, 1.01 mmol) in THF (8 mL). The mixture was then heated at 60° C. for 8 h, cooled to ambient temperature, quenched with aqueous saturated NH4Cl (20 mL), extracted with EtOAc (100 mL), dried with (MgSO4), concentrated, and purified by column chromatography (10% ether in hexane) to afford 4-(6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-1H-benzo[g]quinolin-1-ylmethyl)benzoic acid methyl ester (120 mg, 58%): 1H NMR (400 MHz, CDCl3) δ 8.10 (½ ABq, 2H, J=8.0 Hz, ArH), 7.48 (½ ABq, 2H, J=8.0 Hz, ArH), 7.08 (s, 1H, ArH), 6.70 (s, 1H, ArH), 5.20 (s, 2H, CH2), 4.51 (s, 3H, CH3), 2.91 (t, 2H, J=7.0 Hz, ring CH2), 2.81 (broad m, 2H, ring CH2), 1.60 (s, 4H, 2CH2), 1.23 (s, 12H, 4CH3).
