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

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.

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

ORD record

ord-3c92972b843041aeb1063f6a9a5739c5

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05716984