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

HRID 1802722Notes

Reaction equation

HRID 1802722 reaction equation
[OH:1][CH:2]([CH3:23])[CH2:3][CH2:4][C:5]1[O:6][C:7]2[C:16]3[CH:15]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13][C:12]=3[CH:11]=[CH:10][C:8]=2[N:9]=1.C[N+]1([O-])CCOCC1.O>C(#N)C>[O:1]=[C:2]([CH3:23])[CH2:3][CH2:4][C:5]1[O:6][C:7]2[C:16]3[CH:15]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13][C:12]=3[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 57781241N-{2-[2-(3-Hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide

Product 1

HCID 57781269N-{2-[2-(3-Oxobutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamideYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of N-{2-[2-(3-hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide (72.0 mg, 0.228 mmol), 4 Å molecular sieves (72 mg), 4-methylmorpholine N-oxide (66.8 mg, 0.570 mmol) and tetra-n-propylammonium perruthenate(VII) (8.0 mg, 0.0228 mmol) in acetonitrile (3 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and 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 (22.2 mg, yield 31%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)
  6. customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f5f27c20c9b941d09819d9a28dbf347f
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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