Reaction #49210

Reaction equation

Compound 94

1-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl}-4-hydroxy-pyrrolidin-1-yl]-6-dimethylamino-hexan-1-one

succinic anhydride

triethylamine

→

compound 96

Succinic acid mono-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-(6-dimethylamino-hexanoyl)-pyrrolidin-3-yl]ester

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherdried in a vacuum at 40° C. overnight
2. 2
   workup.DISSOLUTIONThe mixture is dissolved in anhydrous dichloromethane (5 mL)
3. 3
   Washwashed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL)
4. 4
   DryingThe organic phase is dried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated to dryness
6. 6
   OtherThe crude product is purified by column chromatography

Procedure

Referring to scheme 25, Compound 94 (1.2 g, 2 mmol) is mixed with succinic anhydride (0.200 g, 2 mmol) and DMAP (0.244 g, 13 mmol) and dried in a vacuum at 40° C. overnight. The mixture is dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.476 g, 0.64 mL, 4 mmol) is added and the solution stirred at room temperature under argon atmosphere for 16 h. It is then diluted with dichloromethane (100 mL) and washed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL). The organic phase is dried over anhydrous sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography to afford compound 96.

Source