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

HRID 883244Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2-{2-[3-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide (155 mg, 0.381 mmol) in methanol (4 mL) was added a 10% palladium-carbon powder (300 mg), and the mixture was stirred at 50° C. for 4 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 (101 mg, yield 84%).

Workup

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

Sources & evidence

ORD record: ord-ada2eb25ab6e4ad5825eaba0901269e8
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236837B2

Reaction notes

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