反应详情

Combine 1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (2.51 g, 5.4 mmol), (1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt (3.07 g, 6.5 mmol), N,N-diisopropylethylamine (4.8 mL, 27.6 mmol), and acetonitrile (70 mL). Heat to reflux. After 18 hours, cool to ambient temperature, dilute the reaction mixture with ethyl acetate, and extract with water and brine. Separate the organic layer, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 305 methanol/ethyl acetate containing concentrated aqueous ammonia 22 mL/3L. Evaporate the product containing fractions to give a residue. Combine the residue and dichloromethane, filter and evaporate in vacuo to give the title compound: Rf=0.17 (silica gel, 30% methanol/ethyl acetate).

1. temperatureHeat to reflux
2. extractionextract with water and brine
3. customSeparate the organic layer
4. dry with materialdry over Na2SO4
5. filtrationfilter
6. customevaporate in vacuo
7. customto give a residue
8. customEvaporate the product
9. additioncontaining fractions
10. customto give a residue
11. filtrationfilter
12. customevaporate in vacuo