N-(4-Methoxybenzylidene)glycine methyl ester → N-((4-Methoxyphenyl)methyl)glycine methyl ester

HRID 722447ノート

反応式

HRID 722447 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

参加物

5

反応物 2

HCID 4193973N-(4-Methoxybenzylidene)glycine methyl esterHCID 4311764Sodium borohydride

生成物 1

HCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

To a solution of 91.3 g (0.441 mol) of [(4-methoxy-benzylidene)-amino]-acetic acid methyl ester in 500 ml of THF and 1000 ml of MeOH, 20 g (0.529 mol) of sodium borohydride is added portionwise at −10 to 0° C. The reaction mixture is stirred for 30 min. at −10 to 0° C. and quenched with sat. NH4Cl. After adding of ice-water, the mixture is concentrated to ¼ of whole volume and extracted with AcOEt. The combined extracts are washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to give (4-methoxybenzylamino)-acetic acid methyl ester; NMR (CDCl3): 1.87 (br s, 1H), 3.41 (s, 2H), 3.73 (s, 3H), 3.74 (s, 2H), 3.8 (s, 3H), 6.86 (d, 2H, J=8.56 Hz), 7.24 (d, 2H, J=8.56 Hz).

後処理

  1. customquenched with sat. NH4Cl
  2. additionAfter adding of ice-water
  3. concentrationthe mixture is concentrated
  4. extractionextracted with AcOEt
  5. washThe combined extracts are washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a9b116057f5043d9acdbe7f7a69de1ee
出典データセット
uspto-grants-2006_11
特許番号
US07138432B1

反応ノート

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