Toluene → 1-Pyrrolidineacetic acid, ethyl ester

HRID 5508

Reaction equation

HRID 5508 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC=CC=1>O1CCCC1>[N:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7748Ethyl bromoacetateHCID 31268Pyrrolidine

Product 1

HCID 2109961-Pyrrolidineacetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-e8381d73f4f9423dbff70d4f1bb4f249
Source dataset
uspto-grants-1993_09
Patent number
US05244997

Linked notes

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