Reacción #164166

Ecuación de reacción

(R)-quinuclidin-3-ol

DCC

Phenyl-(3-trifluoromethoxy-phenylamino)-acetic acid hydrochloride

HOBT

→

title compound

Rendimiento 86.0%

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

Rendimiento 86.0%

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

Procedimiento

PS-DCC (920 mg, 1.15 mmol, loading: 1.25 mmol/g) is suspended in THF (15 mL). Phenyl-(3-trifluoromethoxy-phenylamino)-acetic acid hydrochloride (I40) (200 mg, 0.57 mmol) and HOBT (176 mg, 1.15 mmol) are added, followed by (R)-quinuclidin-3-ol (219 mg, 1.73 mmol) and the mixture is shaken for 16 hours at RT. 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 to give the title compound as a colorless oil (206 mg, 85% yield, mixture of diastereoisomers).

Fuente