N-(2-{2-[4-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide → N-{2-[2-(4-Hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide

HRID 883243Notes

Reaction equation

HRID 883243 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[O:14][C:15]2[C:24]3[CH:23]([CH2:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][C:16]=2[N:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[O:14][C:15]2[C:24]3[CH:23]([CH2:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

4

Reactant 1

HCID 57781245N-(2-{2-[4-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide

Product 1

HCID 57781243N-{2-[2-(4-Hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamideYield 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-{2-[4-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide (79.5 mg, 0.196 mmol) in methanol (2 mL) was added a 10% palladium-carbon powder (160 mg), and the mixture was stirred at room temperature for 6 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (50.0 mg, yield 81%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-5117c496f7ce42a4a939f270116ce86b
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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