Acetic Acid → Ethyl 3-(benzylamino)butanoate

HRID 515441

Reaktionsgleichung

Reaktionsgleichung von HRID 515441
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH:6]([NH2:8])[CH3:7])[CH3:2].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH:6]([NH:8][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:7])[CH3:2]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 98103Ethyl 3-aminobutyrateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 236384Ethyl 3-(benzylamino)butanoateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-butyric acid ethyl ester (5.00 g, 34.3 mmol), benzaldehyde (4.1 mL, 40 mmol) and acetic acid (1.9 mL, 34 mmol) in 1,2-dichloroethane (120 mL) was added sodium triacetoxyborohydride (17 g, 80 mmol) at room temperature and the mixture was stirred for 20 hours. The reaction mixture was poured into sodium bicarbonate saturated aqueous solution and extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant) to afford 3-benzylamino-butyric acid ethyl ester (2.1 g, 9.5 mmol, 28%) as colorless oil.

Aufarbeitung

  1. extractionextracted with chloroform
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant)

Quellen und Nachweise

ORD-Eintrag
ord-e28b2dda4937418d832f3e1e1ba2e721
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108957B2

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