反应详情

To a solution of 150 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol and 0.176 mL of NEt3 in 4 mL DCM 0.1 mL of isobutyrylchloride was added at 0° C. The yellow reaction mixture was stirred for 3 h at rt and then quenched with sat. aq. NaHCO3. The product was extracted with DCM, the organic phase was evaporated to dryness. The residue was dissolved in EtOAc, silica gel and a few drops of MeOH were added and the mixture was stirred vigorously for 5 h. The mixture was filtered, the filtrate evaporated and the residue purified by CC with EtOAc-MeOH (3:1) to yield 86 mg of pure rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as colorless foam.

1. customquenched with sat. aq. NaHCO3
2. extractionThe product was extracted with DCM
3. customthe organic phase was evaporated to dryness
4. dissolutionThe residue was dissolved in EtOAc
5. additionsilica gel and a few drops of MeOH were added
6. stirringthe mixture was stirred vigorously for 5 h
7. filtrationThe mixture was filtered
8. customthe filtrate evaporated
9. customthe residue purified by CC with EtOAc-MeOH (3:1)