{4-[4-(2-Benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amine → 2-{5-Methyl-2-[4-(methyl-phenyl-amino)-phenyl]-oxazol-4-yl}-ethanol

HRID 1181025Notes

Reaction equation

HRID 1181025 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])C1C=CC=CC=1.[H][H]>C1COCC1.CCO.[Pd]>[CH3:16][C:15]1[O:14][C:13]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[N:12][C:11]=1[CH2:10][CH2:9][OH:8]

Participants

6

Reactant 2

HCID 17984359{4-[4-(2-Benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 179843392-{5-Methyl-2-[4-(methyl-phenyl-amino)-phenyl]-oxazol-4-yl}-ethanolYield 60.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {4-[4-(2-benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amine (195 mg, 0.490 mmol) in THF (2 mL) and EtOH (10 mL) was treated a slurry of Pd/C (200 mg) in EtOH (2 mL). The resulting mixture was treated with hydrogen under balloon pressure for 14 h and filtered through a pad of Celite. The filtrate was concentrated, and crude product was purified by silica gel chromatography column (50% EtOAc/hexanes) to yield the title compound (91 mg, 60%).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customcrude product was purified by silica gel chromatography column (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dfe5a75bd7564626b5956436bcd05333
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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