Reaction Steps
A solution of 6-(benzyloxy)-7-methoxy-2-(3-(triisopropylsilyloxy)benzyl)-1,2,3,4-tetrahydroisoquinoline (2.7 g, 5 mmol) in THF (50 mL) was cooled to 0° C. and 1M TBAF/THF (5.5 mL, 5.5 mmol) added drop wise. The solution was stirred at 0 C. for 1 h 30 min and water (20 mL) added as well as EtOAc (80 mL). The organic layer was washed with water, brine, dried with MgSO4, filtered and concentrated under reduced pressure. The resulting solid was washed with hexane, filtered and dried. 1.7 g (90%), white powder, mp=78-79° C.; Rf: 0.12 (Hexane/EtOAc 3:1), 1H NMR (270 MHz, CDCl3) δ 2.63-2.78 (4H, m, 2×CH2), 3.52 (2H, s, CH2), 3.58 (2H, s, CH2), 3.79 (3H, s, CH3O), 5.08 (2H, s, OCH2), 6.48 (1H, s, ArH), 6.60 (1H, s, ArH), 6.68 (1H, dd, J 8.2 and 2.5 Hz, ArH), 6.82 (1H, d, J 2.5 Hz, ArH), 6.88 (1H, d, J 7.7 Hz, ArH), 7.15 (1H, dd, J 8.2 and 7.7 Hz, 1H, ArH), 7.26-7.47 (5H, m, ArH). 13C NMR (67.5 MHz, CDCl3) δ 12.7((CH3)2CHSi), 18.0 ((CH3)2CHSi), 28.8 (CH2), 50.7 (CH2), 55.9 (CH2), 56.1 (CH3O), 62.7 (CH2), 71.2 (OCH2), 110.1 (CH(Ar)), 114.3 (CH(Ar)), 118.6 (CH(Ar)), 120.8 (CH(Ar)), 126.4 (C(Ar)), 127.4 (CH(Ar)), 127.6 (C(Ar)), 127.8 CH(Ar)), 128.6 (CH(Ar)), 129.2 (CH(Ar)), 137.4 (C(Ar)), 140.0 (C(Ar)), 146.6 (C(Ar)), 147.9 (C(Ar)) and 156.1 (C(Ar)). LC/MS (APCI+) tr=5.12 min m/z 376.59 (M++H); MeOH/H2O 50/50 to 95/5 (5 min); HPLC tr=3.26 min (100%). (CH3CN/H2O 90/10)
