反应详情

PS-DCC (962 mg, 1.37 mmol, loading: 1.33 mmol/g) is suspended in THF (10 mL). HOBT (210 mg, 1.37 mmol), (2-ethyl-phenylamino)-phenyl-acetic acid hydrochloride (160) (200 mg, 0.68 mmol), and (R)-quinuclidin-3-ol (262 mg, 2.06 mmol) are added and the mixture is shaken at RT overnight. PS-DCC is filtered off and washed with THF and the filtrate is evaporated under reduced pressure. The resulting residue is dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer is separated, dried over Na2SO4, filtered and evaporated. The residue is first purified by flash chromatography (DCM/MeOH=9/1) and then by preparative HPLC. The fractions containing the product are pooled, concentrated under vacuum, basified with sat. NaHCO3 and extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and evaporated to afford the title compound as a colorless oil (52 mg, 21% yield, mixture of diastereoisomers).

1. filtrationPS-DCC is filtered off
2. washwashed with THF
3. customthe filtrate is evaporated under reduced pressure
4. dissolutionThe resulting residue is dissolved in EtOAc
5. washwashed with sat. NaHCO3, water and brine
6. customThe organic layer is separated
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. customThe residue is first purified by flash chromatography (DCM/MeOH=9/1)
11. additionThe fractions containing the product
12. concentrationconcentrated under vacuum
13. extractionextracted with EtOAc
14. dry with materialThe organic layer is dried (Na2SO4)
15. filtrationfiltered
16. customevaporated