反应详情

11-Benzyl-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (3.00 g, 10.2 mmol) was stirred at 0° C. in CH2Cl2 (10 mL) and AcOH (5 mL) and treated with bromine (3.21 g, 20 mmol) in CH2Cl2 (10 mL) and AcOH (5 mL). After 18 hours the reaction was quenched with 20% aq. NaHSO3 soln. (100 mL). The product was extracted with CH2Cl2 (3×40 mL) and washed with sat. aq. NaHCO3 soln. (3×50 mL). The combined organic layer was dried through a cotton plug, concentrated and chromatographed on Silica gel to provide an oil (1.05 g, 28%). (TLC 30% EtOAc/hexanes Rf 0.48). 1H NMR (CDCl3) δ 7.13 (m, 3H), 6.91 (m, 3H), 6.68 (d, J=8.0 Hz, 1H), 3.90 (s, 3H), 3.36 (s, 2H), 2.86-2.79 (4H), 2.67 (br d, J=9.0 Hz, 1H), 2.31 (br s, 1H), 2.28 (br s, 1H), 2.22 (br s, 1H), 1.78 (AB d, J=13.0 Hz, 2H). GCMS m/e 373, 371 (M+).

1. customAfter 18 hours the reaction was quenched with 20% aq. NaHSO3 soln
2. extractionThe product was extracted with CH2Cl2 (3×40 mL)
3. washwashed with sat. aq. NaHCO3 soln
4. customThe combined organic layer was dried through a cotton plug
5. concentrationconcentrated
6. customchromatographed on Silica gel