反应详情

1-(3,4-Dichlorobenzyl)-7-methoxy-3,4-dihydronaphthalen-2(1H)-one (5.5 g, 16.4 mmol, example 1), pyrrolidine (1.40 g, 19.7 mmol), and p-toluenesulfonic acid monohydrate (31.0 mg, 0.164 mmol) were dissolved in toluene (100 ml) and refluxed for 2 h using a DeanStark condenser. The solvent was removed and after addition of MeOH (50 ml) and sodium cyanohydride (1.57 g, 24.6 mmol) the mixture was stirred for 4d at room temperature under nitrogen. Water was added, the organic phase separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were washed with saturated NaCl solution, dried over MgSO4, and concentrated to afford a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl23:97→5:95). The beige solid product (1.6 g, 25%) was obtained from precipitation in ethyl acetate/diisopropylether (1:1).

1. temperaturerefluxed for 2 h
2. customThe solvent was removed
3. customthe organic phase separated
4. extractionthe aqueous phase extracted with ethyl acetate
5. washThe combined organic layers were washed with saturated NaCl solution
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customto afford a residue that
9. customwas purified by flash chromatography (silica gel, MeOH/CH2Cl23:97→5:95)