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

HRID 1099201노트

반응식

HRID 1099201 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ef507f4134c54b9393b96459eb7471b9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143405B2

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