Réaction #49184

Équation de réaction

MeOH CHCl3

Amine

5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-ol

triethyl amine

compound 43a

6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic acid pentafluorophenyl ester

→

2-(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrewas brought to ambient temperature
2. 2
   Lavagewashed with 5% NaOH solution (3×50 mL)
3. 3
   SéchageThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated to dryness
6. 6
   AutreUpon purification over silica gel compound 44a
7. 7
   Autrewas obtained as foamy white solid in good yield

Mode opératoire

Amine 38 (9.32 g, 22.2 mmol) and triethyl amine (4.55 g, 6.27 mL, 45 mmol) weres dissolved in anhydrous dichloromethane (20 mL) and cooled to 0° C. under argon. To that solution was added compound 43a (9.5 g, 22.2 mmol) at 0° C. The reaction mixture was brought to ambient temperature and stirred further. After 30 mins, disappearance of starting materials were ascertained by TLC. (10% MeOH/CHCl3). The reaction mixture was diluted with dichloromethane (100 mL) and washed with 5% NaOH solution (3×50 mL) followed by water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Upon purification over silica gel compound 44a was obtained as foamy white solid in good yield. (13.2 g, 89%).

Source