反应详情

To a solution of (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (1.636 g, 5 mmol), prepared as described in Example 1B, in DCE (16 mL) at RT was added benzaldehyde (1 mL, 10 mmol), followed by NaBH(OAc)3 (2.97 g, 14 mmol) and AcOH (0.6 mL, 10 mmol). The reaction mixture was stirred at RT for 16 h, then quenched with aqueous NaHCO3 (40 mL) and extracted with CH2Cl2 (50 mL×3). The combined extracts were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with 0-20% of EtOAc in hexanes to give the title compound (1.70 g, 81%) as a white foam.

1. customquenched with aqueous NaHCO3 (40 mL)
2. extractionextracted with CH2Cl2 (50 mL×3)
3. washThe combined extracts were washed with saturated aqueous NaCl
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customThe resulting residue was chromatographed (silica gel)
7. washeluting with 0-20% of EtOAc in hexanes