Reaction #49184

Reaction equation

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

Solvents

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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