Reaction #7644

Reaction equation

2-aminobutanoic acid

chlorotrimethylsilane

cyclopentanecarbonyl chloride

triethylamine

→

2-[(Cyclopentylcarbonyl)amino]butanoic acid

Solvents

dichloromethane

water

water

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred for 1 hour at room temperature and 1 hour at 40° C
2. 2
   TemperatureAfter cooling down at −10° C.
3. 3
   workup.STIRRINGThe reaction mixture is stirred for 2 hours at −10° C.
4. 4
   Other1 hour
5. 5
   Otherat room temperature
6. 6
   Filtrationfiltered
7. 7
   Washthe solid product washed with water/dichloromethane 9/1, toluene and diethylether

Procedure

35 g (339 mmol) 2-aminobutanoic acid and 75.6 g (747 mmol) triethylamine are suspended in 300 ml of dichloromethane and stirred at 0° C. 81 g (747 mmol) chlorotrimethylsilane are added dropwise, then the mixture is stirred for 1 hour at room temperature and 1 hour at 40° C. After cooling down at −10° C., 45 g (339 mmol) cyclopentanecarbonyl chloride are added slowly. The reaction mixture is stirred for 2 hours at −10° C. and then 1 hour at room temperature. At 0° C., 50 ml of water are added. The mixture is diluted with water and dichloromethane, filtered and the solid product washed with water/dichloromethane 9/1, toluene and diethylether.

Source