反应详情

A solution of 3-bromobenzoic acid (4.0 g, 20 mmol) and EDC (3.83 g, 20 mmol) in 50 mL acetonitrile was added dropwise to a solution of (3R)-(+)-3-aminopyrrolidine (1.72 g, 20 mmol) in 100 mL acetonitrile. The reaction mixture was stirred at room temperature for 2 h and the solvent was removed. The residue was dissolved in 50 mL CH2Cl2 and washed with brine (50 mL). The organic phase was dried (MgSO4) and the solvent was removed. The crude product was purified by silica gel column chromatography (Rf=0.22, CH2Cl2/MeOH, 75:15) to give 3-bromo-N-pyrrolidin-3-yl-benzamide as a colorless solid (2.0 g, 37%). To a solution of the above precursor (1.14 g, 4.24 mmol) in 30 mL CH2Cl2 were added di-tert-butyldicarbonate (925 mg, 4.24 mmol) and triethylamine (596 μl, 4.24 mmol). The reaction mixture was stirred at room temperature for 1 h. The solvent was removed and the crude product was purified by silica gel column chromatography (Rf=0.66, CH2Cl2/MeOH, 90:10) to afford the title intermediate compound 106, as a viscous, colorless oil (1.1 g, 70%). MS (ESI+) m/z=369/371.

1. customthe solvent was removed
2. dissolutionThe residue was dissolved in 50 mL CH2Cl2
3. washwashed with brine (50 mL)
4. dry with materialThe organic phase was dried (MgSO4)
5. customthe solvent was removed
6. customThe crude product was purified by silica gel column chromatography (Rf=0.22, CH2Cl2/MeOH, 75:15)