Ethyl(RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylate → 1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 862342Notes

Reaction equation

HRID 862342 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:11]3[C:25]([O-:27])=[O:26])=[CH:4][C:3]=2[O:2]1.C1OC2C=CC(C3C4C(=CC=CC=4)C(C4C=CC=CC=4)=C3C(OCC)=O)=CC=2O1>CCO.[Pd]>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:11]3[C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 2

HCID 18969642Ethyl(RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylateHCID 217147891-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylate

Product 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acidYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Ethyl (1RS, 2SR, 3SR)-1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylate. To a solution of ethyl (RS)-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate (1.00 g, 2.60 mmol) in EtOH (25 ml) was added 10% palladium on activated carbon (30 mg). The resulting suspension was stirred under an atmosphere of H2 overnight. Thin layer chromatographic analysis indicated that the reaction was incomplete, so additional 10% palladium on activated carbon (30 mg) was added, and the mixture was shaken on a Parr hydrogenator at 30 psi H2 for 2 d. At this time, thin layer chromatographic analysis again indicated that the reaction was incomplete. The reaction mixture was filtered through a pad of Celite, and 10% palladium on activated carbon (250 mg) was added. The reaction mixture was shaken on a Parr hydrogenator at 60 psi H2 overnight. Filtration and repetition of the latter hydrogenation conditions led to complete consumption of starting material. The reaction mixture was filtered through a pad of Celite, and the filtrate was concentrated under reduced pressure to afford the title compound (650 mg, 65%), which was used without further purification.

Workup

  1. stirringthe mixture was shaken on a Parr hydrogenator at 30 psi H2 for 2 d
  2. filtrationThe reaction mixture was filtered through a pad of Celite, and 10% palladium on activated carbon (250 mg)
  3. additionwas added
  4. stirringThe reaction mixture was shaken on a Parr hydrogenator at 60 psi H2 overnight
  5. filtrationFiltration and repetition of the latter hydrogenation conditions
  6. customled to complete consumption of starting material
  7. filtrationThe reaction mixture was filtered through a pad of Celite
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c92972b843041aeb1063f6a9a5739c5
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

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