Réaction #164166

Équation de réaction

(R)-quinuclidin-3-ol

DCC

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

HOBT

→

title compound

Rendement 86.0%

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

Rendement 86.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   FiltrationPS-DCC is filtered off
2. 2
   Autrethe filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   Lavagewashed with water, sat. NaHCO3, water and brine
5. 5
   SéchageThe organic phase is dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated

Mode opératoire

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).

Source