Diethyl Ether → 2-[2-(4-Fluorophenyl)acetyl]4-methoxy-pyrazolidine-1-carboxylic acid benzyl ester

HRID 22693

Reaktionsgleichung

Reaktionsgleichung von HRID 22693
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[CH3:29]COCC>CN(C)C=O.[Ag]=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][CH3:29])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 207247442-[2-(4-Fluorophenyl)acetyl]-4-hydroxypyrazolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 207247452-[2-(4-Fluorophenyl)acetyl]4-methoxy-pyrazolidine-1-carboxylic acid benzyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-[2-(4-Fluorophenyl)acetyl]-4-hydroxy-pyrazolidine-1-carboxylic acid benzyl ester, 28, (2.55 g, 7.91 mmol) is dissolved in dimethylformamide (40 mL). Methyl iodide (1.97 mL, 31.6 mmol) is added followed by silver oxide (3.67 g, 15.8 mmol). The flask is cover with foil and stirred overnight in the absence of light. The reaction mixture is poured into ether (150 mL). The mixture is stirred vigorously at room temperature and filtered through a pad of Celite. The filtrate is washed with water (2×150 mL) and brine (150 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 2.58 g (97% yield) of the desired product as a yellow, clear oil.

Aufarbeitung

  1. stirringThe mixture is stirred vigorously at room temperature
  2. filtrationfiltered through a pad of Celite
  3. washThe filtrate is washed with water (2×150 mL) and brine (150 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-753ae2739ad741178e4c270cf4e13deb
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849627B2

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