反応 #164168

反応方程式

DCC

HOBT

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

(R)-quinuclidin-3-ol

→

title compound

収率 30.0%

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

収率 30.0%

溶媒

THF

反応条件

後処理

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

実験手順

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).

出典