Benzaldehyde → methyl (2R)-2-(benzylamino)propanoate

HRID 355443노트

반응식

HRID 355443 반응식
[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH2:5].C([O-])(=O)C.[Na+].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH:5][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 89020methyl D-alaninateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 10987118methyl (2R)-2-(benzylamino)propanoate수율 59.6%

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

D-Alanine methyl ester (4 g, 28.66 mmol) is taken up in methanol (100 mL). To this is added sodium acetate (5.88 g, 71.65 mmol) and benzaldehyde (2.9 mL, 28.66 mmol). The mixture is stirred for 15 minutes and then a solution of sodium cyanoborohydride (1.08 g, 17.2 mmol) in methanol (5 mL) is added dropwise to the mixture. After stirring for 2 hours methanol is evaporated under reduced pressure and the product is extracted into ether and washed with water (2×). The crude product is purified by silica gel flash chromatography (8:2 hexane:ethyl acetate) to give 3.3 g of N-benzyl D-alanine methyl ester as an oil.

후처리

  1. customis evaporated under reduced pressure
  2. extractionthe product is extracted into ether
  3. washwashed with water (2×)
  4. customThe crude product is purified by silica gel flash chromatography (8:2 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-d51e808d470d484fba0e0f7eeb603f79
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830915

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