HCID 58136544, compound → HCID 58136508, compound

HRID 877167Notes

Reaction equation

HRID 877167 reaction equation
C([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12]([CH3:22])([C:18]([O:20][CH3:21])=[O:19])[CH2:13]2)C1C=CC=CC=1>[Pd].CO>[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12]([CH3:22])([C:18]([O:20][CH3:21])=[O:19])[CH2:13]2

Participants

4

Reactant 1

HCID 58136544HCID 58136544, compound

Product 1

HCID 58136508HCID 58136508, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

At room temperature, 50 mg of palladium on carbon (10%) were added to a solution of 860 mg (2.91 mmol) of methyl 4-(benzylamino)-2-methyl-2,3-dihydro-1H-indene-2-carboxylate in 84 ml of methanol, and the mixture was hydrogenated under atmospheric pressure overnight. After the reaction had gone to completion, the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→1:1). This gave 483 mg (2.35 mol, 81% of theory) of a colorless solid.

Workup

  1. customwas hydrogenated under atmospheric pressure overnight
  2. filtrationthe reaction solution was filtered through kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-481703ce41c74e70ae3f929b4bce5935
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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