反应 #164187

反应方程式

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

HOBT

DCC

(R)-quinuclidin-3-ol

→

title compound

收率 38.0%

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

收率 38.0%

溶剂

dioxane

反应条件

后处理

1. 1
   过滤The white precipitate is filtered
2. 2
   其他is evaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue is dissolved in EtOAc
4. 4
   洗涤washed with sat. Na2CO3
5. 5
   干燥The organic phase is dried over sodium sulphate
6. 6
   过滤filtered
7. 7
   其他evaporated to dryness
8. 8
   其他The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5)

实验过程

(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).

来源