2-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl ester → 2,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

HRID 22683

Reaction equation

HRID 22683 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][N:12]1[C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=O)C1C=CC=CC=1>CO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:23]([N:12]2[CH2:13][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:15][NH:11]2)=[O:32])=[CH:26][CH:27]=1

Participants

3

Reactant 1

HCID 207247472-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl ester

Product 1

HCID 207247362,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl esterYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy)-pyrazolidine-1-carboxylic acid 1-benzyl ester, 31, (1.71 g, 3.86 mmol) is dissolved in methanol (40 mL). The flask is flushed with nitrogen and charged with 10% palladium on carbon (300 mg). The reaction flask is stirred vigorously at room temperature under 1 atmosphere of hydrogen gas for 6 hours. The flask is flushed with nitrogen and the reaction mixture filtered through a pad of Celite, rinsing with ethyl acetate (100 mL). The filtrate is concentrated in vacuo to afford 1.18 g (98% yield) of the desired product as a tan solid.

Workup

  1. customThe flask is flushed with nitrogen
  2. additioncharged with 10% palladium on carbon (300 mg)
  3. customThe flask is flushed with nitrogen
  4. filtrationthe reaction mixture filtered through a pad of Celite
  5. washrinsing with ethyl acetate (100 mL)
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-6faa06678e3c4fe4a4121020dbf05d10
Source dataset
uspto-grants-2005_02
Patent number
US06849627B2

Linked notes

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