Reacción #164168

Ecuación de reacción

DCC

HOBT

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

(R)-quinuclidin-3-ol

→

title compound

Rendimiento 30.0%

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

Rendimiento 30.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónPS-DCC is filtered off
2. 2
   Otrothe filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   Lavadowashed with water, sat. NaHCO3, water and brine
5. 5
   SecadoThe organic phase is dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe crude is purified by flash chromatography (DCM/MeOH=95/5)

Procedimiento

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).

Fuente