Reaction Steps
To a solution of 6,6,9,9-tetramethyl-1,2,3,4,6,7,8,9-octahydrobenzo[g]quinoline (200 mg, 0.823 mmol) in THF (4 mL) was added NaH (30 mg, 1.2 mmol) in one portion at ambient temperature. To this solution was added methyl 4-(bromomethyl)-benzoate (377 mg, 1.6 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 (MgSO4), concentrated, and purified by column chromatography (10% ether in hexanes) to afford 4-(6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-2H-benzo[g]quinolin-1-ylmethyl)-benzoic acid methyl ester 130 mg (40%): 1H NMR (400 MHz, CDCl3) δ 7.98(½ ABq, 2H, J=9.0 Hz, ArH), 7.38(½ ABq, 2H, J=9.0 Hz, ArH), 6.91(s, 1H, ArH), 6.3(s, 1H, ArH) 4.45(s, 2H, CH2), 3.90(s, 3H, CH3), 3.2(t, 2H, J=5.4 Hz, ring CH2), 2.79(t, 2H, J=6.4 Hz, ring CH2), 2.02(m, 2H, ring CH2), 1.59(s, 4H, 2CH2), 1.22(s, 6H, 2CH3), 1.06(s, 6H, 2CH3).
