反应详情

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (1.87 g, 5.68 mmol), allyl methanesulfonylethyl ether (1.83 g, 10.1 mmol), and potassium carbonate (1.60 g, 11.5 mmol) in acetone (21 mL) and water (7 mL). Heat to reflux. After 18 hours, concentrate the reaction mixture in vacuo to remove most of the acetone. Partition the concentrated reaction mixture between ethyl acetate and water. Separate the aqueous layer and extract three times with ethyl acetate. Extract the combined organic layers with saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 15% ethyl acetate/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine: Rf=0.48 (silica gel, 20% ethyl acetate/dichloromethane).

1. temperatureHeat to reflux
2. concentrationconcentrate the reaction mixture in vacuo
3. customto remove most of the acetone
4. customPartition
5. customthe concentrated reaction mixture between ethyl acetate and water
6. customSeparate the aqueous layer
7. extractionextract three times with ethyl acetate
8. extractionExtract the combined organic layers with saturated aqueous sodium chloride solution
9. dry with materialDry the organic layer over Na2SO4
10. filtrationfilter
11. customevaporate in vacuo
12. customto obtain a residue