反应详情

Combine 1-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (1.70 g, 5.4 mmol) in tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice bath. Add sodium hydride (0.32 g, 60% in oil, 8.1 mmol) portionwise. After 15 minutes, warm to ambient temperature. After about 30 minutes, when the gas evolution ceases, add 2-(chloromethyl)furan (0.94 g, 8.1 mmol). After 18 hours, cool in an ice bath, add ice and then a saturated aqueous solution of ammonium chloride. Evaporate the reaction mixture to remove most of the tetrahydrofuran, dilute with ethyl acetate and extract with a saturate aqueous solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 50% ethyl acetate/hexane to give 1-t-butoxycarbonyl-4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.47 (silica gel, ethyl acetate).

1. temperatureCool in an ice bath
2. waitAfter about 30 minutes
3. waitAfter 18 hours
4. temperaturecool in an ice bath
5. additionadd ice
6. customEvaporate the reaction mixture
7. customto remove most of the tetrahydrofuran
8. additiondilute with ethyl acetate
9. extractionextract with a saturate aqueous solution of sodium bicarbonate
10. dry with materialDry the organic layer over Na2SO4
11. filtrationfilter
12. customevaporate in vacuo
13. customto give a residue