反应详情

To a solution of 4-fluorobenzaldehyde (496 mg, 4.00 mmol) in a mixed solvent of CH2Cl2 (10 mL) and 2-propanol (2 mL) at rt was added tert-butyl 4-(aminomethyl)benzylcarbamate (945 mg, 4.00 mmol, Aldrich). The reaction mixture was stirred at rt overnight. The next morning, sodium borohydride (296 mg, 8.0 mmol) was added, and the mixture was stirred at rt for 2 h. The reaction mixture was quenched by adding 3 mL of MeOH and 3 mL of saturated aq NaHCO3. The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried, concentrated and purified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc to give the title compound (0.69 g, 48%) as a viscous material. MS (ESI): 345.1 (M+H)+.

1. stirringthe mixture was stirred at rt for 2 h
2. customThe reaction mixture was quenched
3. additionby adding 3 mL of MeOH and 3 mL of saturated aq NaHCO3
4. extractionThe mixture was extracted with EtOAc (3×50 mL)
5. customThe combined organic extracts were dried
6. concentrationconcentrated
7. custompurified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc