2-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid → 2-[2-(3-Methoxy-propyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]=[CH:5][C:6]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=1[C:8]([NH:10][C:11]1([C:20]([OH:22])=[O:21])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:9]>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=1[C:8]([NH:10][C:11]1([C:20]([OH:22])=[O:21])[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19]1)=[O:9]Participants
4
Procedure
To a solution of 2-[2-(3-methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid (229) (120 mg, 0.34 mmol) in absolute EtOH (15 mL) is added the catalyst, Pd—C (5 wt. % Pd, 93 mg, 4.4% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 50° C., overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (222) as white solid (80 mg, 49%).