Reaktion #164168

Reaktionsgleichung

DCC

HOBT

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

(R)-quinuclidin-3-ol

→

title compound

Ausbeute 30.0%

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

Ausbeute 30.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationPS-DCC is filtered off
2. 2
   Sonstigethe filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   Waschenwashed with water, sat. NaHCO3, water and brine
5. 5
   TrocknenThe organic phase is dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe crude is purified by flash chromatography (DCM/MeOH=95/5)

Vorschrift

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).

Quelle