Acetic Acid → Ethyl 3-(benzylamino)butanoate

HRID 515441ノート

反応式

HRID 515441 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 236384Ethyl 3-(benzylamino)butanoate収率 28%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e28b2dda4937418d832f3e1e1ba2e721
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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