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

HRID 883240Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2-{2-[(benzyloxy)methyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide (50.0 mg, 0.131 mmol) in methanol (1 mL) was added a 10% palladium-carbon powder (100 mg), and the mixture was stirred at 50° C. for 24 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) and recrystallized (ethyl acetate/hexane) to give the title compound (19.0 mg, yield 53%).

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)
customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-71d6fc54b6a741019c3779458e818512
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236837B2

Reaction notes

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