N-(4-Methoxybenzylidene)glycine methyl ester → N-((4-Methoxyphenyl)methyl)glycine methyl ester

HRID 722447Notes

Reaction equation

HRID 722447 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 4193973N-(4-Methoxybenzylidene)glycine methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 91.3 g (0.441 mol) of [(4-methoxy-benzylidene)-amino]-acetic acid methyl ester in 500 ml of THF and 1000 ml of MeOH, 20 g (0.529 mol) of sodium borohydride is added portionwise at −10 to 0° C. The reaction mixture is stirred for 30 min. at −10 to 0° C. and quenched with sat. NH4Cl. After adding of ice-water, the mixture is concentrated to ¼ of whole volume and extracted with AcOEt. The combined extracts are washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to give (4-methoxybenzylamino)-acetic acid methyl ester; NMR (CDCl3): 1.87 (br s, 1H), 3.41 (s, 2H), 3.73 (s, 3H), 3.74 (s, 2H), 3.8 (s, 3H), 6.86 (d, 2H, J=8.56 Hz), 7.24 (d, 2H, J=8.56 Hz).

Workup

  1. customquenched with sat. NH4Cl
  2. additionAfter adding of ice-water
  3. concentrationthe mixture is concentrated
  4. extractionextracted with AcOEt
  5. washThe combined extracts are washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9b116057f5043d9acdbe7f7a69de1ee
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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