2-[2-(4-Fluorophenyl)acetyl]-4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester HCl salt → 2-(4-Fluorophenyl)-1-(4-morpholin-4-yl-pyrazolidin-1-yl)ethanone

HRID 2052858Notes

Reaction equation

HRID 2052858 reaction equation
Cl.C(OC([N:12]1[CH2:16][CH:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:14][N:13]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.[Pd]>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:23]([N:13]2[CH2:14][CH:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:16][NH:12]2)=[O:32])=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 692195562-[2-(4-Fluorophenyl)acetyl]-4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester HCl salt

Product 1

HCID 219922062-(4-Fluorophenyl)-1-(4-morpholin-4-yl-pyrazolidin-1-yl)ethanoneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[2-(4-Fluorophenyl)acetyl]-4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester HCl salt, 12, (100 mg, 0.2 mmol) is dissolved in methanol and Pd/C (5 mg) is added. The solution is then hydrogenated in a Parr® Hydrogenation Apparatus for 3 days after which time the catalyst is removed by filtration and the filtrate concentrated in vacuo to afford 55 mg (81% yield) of the desired product as a tan solid.

Workup

  1. customafter which time the catalyst is removed by filtration
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d6efa7f2f82e4d7e85225d6245b9a5dc
Source dataset
uspto-grants-2008_02
Patent number
US07326714B2

Reaction notes

Loading…