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

HRID 722447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722447
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a9b116057f5043d9acdbe7f7a69de1ee
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138432B1

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