Benzyl Bromide → (S)-methyl 2-(benzylamino)propanoate

HRID 1038557Notes

Reaction equation

HRID 1038557 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([NH:6][C@@H:5]([CH3:7])[C:4]([O:3][CH3:2])=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 10535780(S)-methyl 2-(benzylamino)propanoateYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

L-alanine methyl ester hydrochloride (15.0 g, 107 mmol) was dissolved in N,N′-dimethylformamide (150 mL), added potassium carbonate (32.5 g, 235 mmol) and benzyl bromide (18.4 g, 107 mmol) and the mixture was stirred at 80° C. overnight. Then, the mixture was reverted to room temperature, the reaction solution was filtered through a pad of celite, extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (12.7 g, 61%) was obtained as a colorless oil.

Workup

  1. customwas reverted to room temperature
  2. filtrationthe reaction solution was filtered through a pad of celite
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f0757a9e1f7943aea966d1074ecc9a34
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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