反应 #164168

反应方程式

DCC

HOBT

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

(R)-quinuclidin-3-ol

→

title compound

收率 30.0%

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

收率 30.0%

溶剂

THF

反应条件

后处理

1. 1
   过滤PS-DCC is filtered off
2. 2
   其他the filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   洗涤washed with water, sat. NaHCO3, water and brine
5. 5
   干燥The organic phase is dried over Na2SO4
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他The crude is purified by flash chromatography (DCM/MeOH=95/5)

实验过程

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).

来源