반응 #164168

반응 방정식

DCC

HOBT

(3-ethyl-phenylamino)-phenyl-acetic acid hydrochloride

(R)-quinuclidin-3-ol

→

title compound

수율 30.0%

(3-ethyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

수율 30.0%

용매

THF

반응 조건

후처리

1. 1
   여과PS-DCC is filtered off
2. 2
   기타the filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   세척washed with water, sat. NaHCO3, water and brine
5. 5
   건조The organic phase is dried over Na2SO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The crude is purified by flash chromatography (DCM/MeOH=95/5)

실험 절차

PS-DCC (1097 mg, 1.371 mmol, loading: 1.25 mmol/g) is suspended in THF (15 mL). HOBT (210 mg, 1.37 mmol), (3-ethyl-phenylamino)-phenyl-acetic acid hydrochloride (I42) (200 mg, 0.68 mmol), and (R)-quinuclidin-3-ol (262 mg, 2.06 mmol) are added and the suspension is shaken at RT for 16 hours. PS-DCC is filtered off and the filtrate is evaporated. The resulting residue is dissolved in EtOAc and washed with water, sat. NaHCO3, water and brine. The organic phase is dried over Na2SO4, filtered and evaporated. The crude is purified by flash chromatography (DCM/MeOH=95/5) to obtain the title compound as a colorless oil (72 mg, 30% yield, mixture of diastereoisomers).

출처