反应详情

((1S,2S)-1-Formyl-2-methyl-butyl)-carbamic acid tert-butyl ester (1.62 g, 7.5 mmol), and 6-bromo-naphthalen-2-ylamine (1.11 g, 5.0 mmol) were combined in DCE (10 mL). After stirring 5 min, NaBH(OAc)3 (2.33 g, 11 mmol) was added. The whole mixture was then stirred at r.t. for 18 h. The reaction mixture was transferred to a separatory funnel containing water (50 mL). The aqueous layer was extracted with DCM (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated. The residue was purified via column chromatography on silica gel (10% ethyl acetate in hexanes) to afford {(1S,2S)-1-[(6-bromo-naphthalen-2-ylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (1.78 g, 85% yield) as an off-white solid. LC/MS (ESI) m/e 423.2 [(M+H)+, calcd for C21H29BrN2O2 421.4].

1. stirringThe whole mixture was then stirred at r.t. for 18 h
2. customThe reaction mixture was transferred to a separatory funnel
3. extractionThe aqueous layer was extracted with DCM (3×50 mL)
4. washThe combined organic layers were washed with brine (50 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified via column chromatography on silica gel (10% ethyl acetate in hexanes)