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

HRID 22668

Reaction equation

HRID 22668 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21908982Water methylene chlorideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-81e393028ae24d67914a3f1a874c6abd
Source dataset
uspto-grants-2005_02
Patent number
US06849627B2

Linked notes

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