反应详情

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (150 mg) (0.38 mmol) in DMF (5 ml) was carefully dropped on a suspension of NaH 60% (18.2 mg) (1.2 eq) in DMF (5 ml) at RT. The reaction mixture was stirred for 1 h at RT, then ethyl bromoacetate (0.052 ml) (1.2 eq) was added. After one night, the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8) to give [7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid ethyl ester (46.5 mg) as a white solid. 1H NMR (CDCl3): 7.55 (2H, d), 7.25 (2H, d), 7.1 (1H, m), 6.8 (2H, m), 5.0 (1H, m), 4.45 (1H, d), 4.2 (2H, q), 3.75 (1H, d), 3.05 (1H, d), 2.90 (1H, d), 2.5-2.1 (2H, m), 2.1-1.8 (4H, m), 1.25 (3H, t).

1. waitAfter one night
2. additionthe reaction mixture was poured on water
3. extractionextracted with tBuOMe
4. washThe organic layer was washed with water
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8)