1-Phenethylamine → N-((1R)-1-Phenylethyl)glycine ethyl ester

HRID 1642159

Reaction equation

HRID 1642159 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][CH:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[C:10]1([C@H:9]([NH:16][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 74081-PhenethylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 6455333N-((1R)-1-Phenylethyl)glycine ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl bromoacetate (4.14 g; 24.8 mmol) was treated with (R) α-methylbenzylamine (3 g, 24.8 mmol) and ethyldiisopropylamine (3.2 g; 24.8 mmol) in toluene (100 mL). After heating at reflux for 18 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane) to provide the title compound (3.2 g, 63% yield). MS (DCI/NH3) m/z 208 (M+H)+.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane)

Sources & evidence

ORD record
ord-5eedbaa1ab04496a94960ab181062da5
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Linked notes

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