Reaction #5604

Reaction equation

toluene

pyrrolidine

ethyl bromoacetate

→

ETHYL 1-PYRROLIDINEACETATE

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature below 30° C
2. 2
   Otherto precipitate pyrrolidinium bromide, which
3. 3
   Otherwas separated by filtration
4. 4
   OtherThe filtrate was evaporated under vacuum
5. 5
   Otherto provide a residue of about 241 g of ethyl 1-pyrrolinidineacetate

Procedure

To an ice bath-cooled solution of 213.4 g (3 mol) of pyrrolidine in 450 mL of tetrahydrofuran was added dropwise over about 2 hours 250.5 g (1.5 mol) of ethyl bromoacetate, maintaining the temperature below 30° C. To this solution was added 150 mL of toluene to precipitate pyrrolidinium bromide, which was separated by filtration. The filtrate was evaporated under vacuum to provide a residue of about 241 g of ethyl 1-pyrrolinidineacetate.

Source