Reaktion #164193

Reaktionsgleichung

(4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

(R)-quinuclidin-3-ol

HOBT

DCC

→

title compound

Ausbeute 50.0%

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

Ausbeute 50.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is evaporated
2. 2
   workup.DISSOLUTIONthe crude is dissolved in EtOAc
3. 3
   Filtrationthe insoluble is filtered off
4. 4
   WaschenThe clear solution is washed with 1N K2CO3
5. 5
   TrocknenThe organic layer is dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe crude is purified by silica gel chromatography (EtOAc/MeOH=8/2)

Vorschrift

A mixture of (4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid (I83) (510 mg, 1.94 mmol), (R)-quinuclidin-3-ol (246 mg, 1.94 mmol), HOBT (356 mg, 2.32 mmol) and DCC (480 mg, 2.32 mmol) in THF (10 mL) is stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent is evaporated, the crude is dissolved in EtOAc and the insoluble is filtered off. The clear solution is washed with 1N K2CO3 and then with brine. The organic layer is dried over Na2SO4, filtered and evaporated. The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2) to give the title compound as a yellow oil (360 mg, 50% yield, mixture of diastereoisomers).

Quelle