반응 #164187

반응 방정식

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid hydrochloride

HOBT

DCC

(R)-quinuclidin-3-ol

→

title compound

수율 38.0%

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

수율 38.0%

용매

dioxane

반응 조건

후처리

1. 1
   여과The white precipitate is filtered
2. 2
   기타is evaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue is dissolved in EtOAc
4. 4
   세척washed with sat. Na2CO3
5. 5
   건조The organic phase is dried over sodium sulphate
6. 6
   여과filtered
7. 7
   기타evaporated to dryness
8. 8
   기타The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5)

실험 절차

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid hydrochloride (I74) (97 mg, 0.35 mmol), HOBT (107 mg, 0.70 mmol), DCC (144 mg, 0.70 mmol) and (R)-quinuclidin-3-ol (89 mg, 0.70 mmol) are dissolved in dioxane (5 mL) and the mixture is stirred at RT for 15 hours. The white precipitate is filtered and discarded whereas the clear solution is evaporated to dryness. The residue is dissolved in EtOAc and washed with sat. Na2CO3 and then brine. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5) to obtain the title compound as a pale yellow oil (46 mg, 38% yield, mixture of diastereoisomers).

출처