反应详情

Combine (1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (4.00 g, 13.87 mmol) and dimethylformamide (12 mL) and tetrahydrofuran (60 mL). Cool in an ice-bath. Add sodium hydride (24 mg, 15.3 mmol). After 24 hours, add 2-(t-butyldimethylsilyloxy) ethyl iodide (3.97 g, 13.87 mmol). After 60 hours, add ice to quench the reaction. Evaporate the quenched reaction mixture in vacuo to remove most of the tetrahydrofuran. Partition the evaporated reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane and then 5% methanol/dichloromethane to give (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.14 (silica gel, 40% ethyl acetate/dichloromethane).

1. temperatureCool in an ice-bath
2. waitAfter 60 hours
3. additionadd ice
4. customto quench
5. customthe reaction
6. customEvaporate
7. customthe quenched reaction mixture in vacuo
8. customto remove most of the tetrahydrofuran
9. customPartition
10. customthe evaporated reaction mixture between water and ethyl acetate
11. customSeparate the layers
12. extractionextract the organic layer three times with water
13. dry with materialDry the organic layer over MgSO4
14. filtrationfilter
15. customevaporate in vacuo
16. customto give a residue