Acetic Acid → Diethyl 1-acetyl-5-hydroxy-3-phenylpyrrolidine-2,2-dicarboxylate

HRID 1099201ノート

反応式

HRID 1099201 の反応式
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[Na].[CH:17](=[O:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C>C(O)C>[C:1]([N:4]1[CH:17]([OH:26])[CH2:18][CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 3073-Phenylprop-2-EnalHCID 14041Acetamidomalonic acid diethyl esterHCID 5360545Sodium

生成物 1

HCID 658963Diethyl 1-acetyl-5-hydroxy-3-phenylpyrrolidine-2,2-dicarboxylate収率 96%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of diethyl acetamidomalonate (75.0 g, 345 mmol) in ethanol (375 ml) at 0° C. was added sodium metal (6.9 g, 36 mmol). Cinnamaldehyde (50.0 g, 378 mmol) was added dropwise to the resulting solution. The reaction was warmed to rt and allowed to stir for 2 h. Acetic acid (7 ml) was added, and the solution was concentrated. The residue was dissolved in EtOAc, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude solid was triturated with hexanes/EtOAc to yield diethyl 1-acetyl-5-hydroxy-3-phenylpyrrolidine-2,2-dicarboxylate as a white solid (96%).

後処理

  1. concentrationthe solution was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was triturated with hexanes/EtOAc

出典と根拠

ORDレコード
ord-ef507f4134c54b9393b96459eb7471b9
出典データセット
uspto-grants-2012_03
特許番号
US08143405B2

反応ノート

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