Ethyl bromoacetate → Glycine, N-cyclopropyl-, ethyl ester

HRID 1413413Notes

Reaction equation

HRID 1413413 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8]1([NH2:11])[CH2:10][CH2:9]1>C(OCC)C>[CH:8]1([NH:11][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 69828Cyclopropylamine

Product 1

HCID 22476174Glycine, N-cyclopropyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl bromoacetate in diethyl ether was added dropwise to a solution cooled to +5° C. of cyclopropylamine in diethyl ether. A white solid formed. The mixture was stirred for 3 hours while maintaining the cooling. The precipitate was filtered off and extracted with ether and the filtrate was evaporated. The residue was triturated with benzene/cyclohexane and the solid was filtered off. The filtrate was evaporated and the residue was distilled and fractionated to give ethyl cyclopropylaminoacetate of boiling point 32°-33° C./0.7 mmHg: nD19 =1.4384.

Workup

  1. customA white solid formed
  2. temperaturewhile maintaining the cooling
  3. filtrationThe precipitate was filtered off
  4. extractionextracted with ether
  5. customthe filtrate was evaporated
  6. customThe residue was triturated with benzene/cyclohexane
  7. filtrationthe solid was filtered off
  8. customThe filtrate was evaporated
  9. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b21cfaa1dadd4113a4846e145dbb6fcf
Source dataset
uspto-grants-1981_02
Patent number
US04250085

Reaction notes

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