Acetic Acid → Ethyl 3-(benzylamino)butanoate

HRID 515441

Reaction equation

HRID 515441 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

HCID 236384Ethyl 3-(benzylamino)butanoateYield 28%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e28b2dda4937418d832f3e1e1ba2e721
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Linked notes

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