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

HRID 355443

反応式

HRID 355443 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 10987118methyl (2R)-2-(benzylamino)propanoate収率 59.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d51e808d470d484fba0e0f7eeb603f79
出典データセット
uspto-grants-1998_11
特許番号
US05830915

関連ノート

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