1-hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester → 1-amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester

HRID 19552Notes

Reaction equation

HRID 19552 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[N:31]O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:31])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 866140261-hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 115967791-amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester (0.5 g, 1.17 mmol) obtained in Step 1 was dissolved in methanol (30 mL) and 10%-palladium (400 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 377 mg of the titled compound (yield: 78%).

Workup

  1. customwhile providing H2 gas
  2. filtrationfiltered through celite
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-73279b7b7baa4c02ba916dbff20a21ca
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

Loading…