反应详情

To 150 mg (0.28 mmol) of amine 7-2 in MeOH was added 145 mg (0.83 mmol) of (t-butyldimethylsilyloxy) acetaldehyde and several drops of HOAc. After stirring for 1 h, 35 mg (0.55 mmol) of NaCNBH3 was added and the reaction was stirred overnight in a sealed flask. The mixture was partitioned between EtOAc and saturated NaHCO3, the layers were separated, the organic phase was washed with water, dried over MgSO4, and concentrated by rotary evaporation. The residue was dissolved in dry EtOAc, saturated with HCl(g) and stirred for 1 h. The reaction was partitioned between EtOAc and saturated NaHCO3, the layers were separated, the organic phase was washed with water, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by reverse phase HPLC, but was not of sufficient purity, so it was then purified by column chromatography on silica gel with 20:1:1 EtOH/NH4OH/H2O in EtOAc to provide 11-1 as a white solid. Data 11-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.3 (s, 1H), 5.4 (m, 1H), 4.8 (m, 1H), 4.6 (m, 1H), 4.4 (m, 1H), 4.0 (m, 1H), 3.75 (m, 1H), 3.6 (m, 2H), 3.0 (m, 2H), 2.9 (s, 3H), 2.5 (m, 2H), 2.2 (m, 2H), 1.8 (m, 3H), 1.7 (m, 1H) ppm. HRMS (ES) calc'd M+H for C26H31F2N3O3: 472.2406. Found: 472.2386.

1. stirringthe reaction was stirred overnight in a sealed flask
2. customThe mixture was partitioned between EtOAc and saturated NaHCO3
3. customthe layers were separated
4. washthe organic phase was washed with water
5. dry with materialdried over MgSO4
6. concentrationconcentrated by rotary evaporation
7. dissolutionThe residue was dissolved in dry EtOAc, saturated with HCl(g)
8. stirringstirred for 1 h
9. customThe reaction was partitioned between EtOAc and saturated NaHCO3
10. customthe layers were separated
11. washthe organic phase was washed with water
12. dry with materialdried over MgSO4
13. concentrationconcentrated by rotary evaporation
14. customThe residue was purified by reverse phase HPLC
15. customwas then purified by column chromatography on silica gel with 20:1:1 EtOH/NH4OH/H2O in EtOAc