Reaktion #43351

Reaktionsgleichung

THF

THF

1-{4-[2-((3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl)ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one

→

title compound

Ausbeute 50.7%

4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3R)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-one

Ausbeute 50.7%

Lösungsmittel

Chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthen was washed with saturated brine
2. 2
   Trocknendried over anhydrous magnesium sulfate
3. 3
   EinengenConcentrating the solvent under reduced pressure
4. 4
   Sonstigethe residue was purified on high performance liquid chromatography (YMC-Pack™ pro C-18, 0.1% THF solution: 0.1% TFA acetonitrile solution=10→95%)
5. 5
   Sonstigethe resulting crude title compound was recrystallized fronm ethyl acetate-heptane mixed solvent

Vorschrift

Tetra-n-butylamnunium fluoroide (1.0M THF solution, 0.924 mL, 0.92 mmol) was added to THF (2 mL) solution of 1-{4-[2-((3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl)ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (257.0 mg, 0.46 mmol), and stirred at room temperature for 3 hours. Chloroform was added to the reaction liquid, which then was washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on high performance liquid chromatography (YMC-Pack™ pro C-18, 0.1% THF solution: 0.1% TFA acetonitrile solution=10→95%), and the resulting crude title compound was recrystallized fronm ethyl acetate-heptane mixed solvent to provide the title compound (103.1 mg, 50%).

Quelle