Sodium Hydroxide → 2-[2-(4-Fluorophenyl)acetyl]4-methylene-pyrazolidine-1-carboxylic acid benzyl ester

HRID 7642

Reaktionsgleichung

Reaktionsgleichung von HRID 7642
[OH-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][C:16](=[CH2:18])[CH2:15][NH:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1>O.C(Cl)Cl.O>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][C:16](=[CH2:18])[CH2:15][N:14]1[C:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 37449884-Fluorophenylacetyl chlorideHCID 12970153Benzyl 4-methylidenepyrazolidine-1-carboxylate

Produkt 1

HCID 129701542-[2-(4-Fluorophenyl)acetyl]4-methylene-pyrazolidine-1-carboxylic acid benzyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

Sodium hydroxide (0.12 g, 3 mmol) is dissolved in a 1:2 water/methylene chloride solution (30 mL) with rapid stirring followed by the addition of 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester, 9, (0.62 g, 2.8 mmol) at room temperature. (4-Fluorophenyl)acetyl chloride (0.39 mL, 4.2 mmol) is added and the reaction is allowed to stir for 18 hours after which time the reaction mixture is diluted with water (10 mL) and the layers allowed to separate. The aqueous layer is extracted with methylene chloride, the organic layers combined, dried, and filtered. Concentration in vacuo affords the crude product which is purified over silica (1:3 ethyl acetate/hexane) to provide 0.54 g (62% yield) of the desired product.

Aufarbeitung

  1. stirringto stir for 18 hours after which time the reaction mixture
  2. customto separate
  3. extractionThe aqueous layer is extracted with methylene chloride
  4. customdried
  5. filtrationfiltered
  6. concentrationConcentration in vacuo
  7. customaffords the crude product which
  8. customis purified over silica (1:3 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-500db76911fe4a4ead497cd52689022e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087615B2

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