2-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid → 2-(2-Cyclopentyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047774Notes

Reaction equation

HRID 1047774 reaction equation
[C:1]1([C:6]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=2[C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH:2]=1>CCO.[Pd]>[CH:1]1([C:6]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=2[C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 251594862-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

Product 1

HCID 251606732-(2-Cyclopentyl-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 50.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(2-cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid (132) (365 mg, 1.01 mmol) in absolute EtOH (15 mL) is added the catalyst, Pd—C (50% wetted powder, 10% Pd, 192 mg, 9% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 50° C., overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed by EtOH. The combined EtOH solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (133) as white solid (184 mg, 50%).

Workup

  1. customThe resulting reaction mixture
  2. custom50 psi, 50° C., overnight
  3. customThe catalyst is removed by the filtration through a pre-column (10 g silica gel)
  4. washwashed by EtOH
  5. concentrationThe combined EtOH solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-032eb6a1c2374ff49cac9dab8b0d330b
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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