Acetic Acid → Ethyl 3-(benzylamino)butanoate

HRID 515441

반응식

HRID 515441 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

HCID 236384Ethyl 3-(benzylamino)butanoate수율 28%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e28b2dda4937418d832f3e1e1ba2e721
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

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