Morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester → Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

HRID 7664Notes

Reaction equation

HRID 7664 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([O:16][C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[CH2:13][N:12]1[C:25](=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=O)C1C=CC=CC=1>CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:25]([N:12]2[CH2:13][CH:14]([O:16][C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:15][NH:11]2)=[O:34])=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 20724738Morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

Product 1

HCID 20724737Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

morpholine-4-carboxylic acid 1-benzyloxycarbonyl-2-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 40, (512 mg, 1.09 mmol) is dissolved in methanol (10 mL) and the flask flushed with nitrogen then charged with 10% palladium on carbon (103 mg). The reaction mixture is vigorously stirred and hydrogenated at 1 atmosphere for 2.5 hours at room temperature. The reaction mixture is filtered through a pad of Celite, rinsed with ethyl acetate (100 mL) and concentrated in vacuo to afford 354 mg of the desired product as a white powder.

Workup

  1. customthe flask flushed with nitrogen
  2. additionthen charged with 10% palladium on carbon (103 mg)
  3. filtrationThe reaction mixture is filtered through a pad of Celite
  4. washrinsed with ethyl acetate (100 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-213fc392fbf14d7a9f55a86e23cd71e9
Source dataset
uspto-grants-2006_08
Patent number
US07087615B2

Reaction notes

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