HCID 489113, compound → HCID 510558, compound

HRID 843166Notes

Reaction equation

HRID 843166 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20]CC3C=CC=CC=3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[H][H]>C1COCC1.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 489113HCID 489113, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 510558HCID 510558, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-benzylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (the compound in Example 98: 180 mg) in THF (10 ml) was added 20% Pd(OH)2 on charcoal catalyst (40 mg) under N2. The nitrogen atmosphere was replaced by hydrogen (1 atom) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered through a pad of celite and the pad of celite was rinsed with methanol and dichloromethane. The filtrate combined was concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane-MeOH) to give 4-(3-amino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (125 mg) as a colorless oil. FAB-MS: m/z 278 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washthe pad of celite was rinsed with methanol and dichloromethane
  3. concentrationThe filtrate combined was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (dichloromethane-MeOH)

Sources & evidence

ORD record
ord-a9d9bce8dfb24c2fb4ddf83dacb5fed9
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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