Methyl morpholine oxide → N-(2-fluoro-4-hexanoylphenyl)-2,2-dimethylpropanamide

HRID 1372500Notes

Reaction equation

HRID 1372500 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[C:6]([C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 17972745HCID 17972745, compound

Product 1

HCID 17972711N-(2-fluoro-4-hexanoylphenyl)-2,2-dimethylpropanamideYield 97%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[2-fluoro-4-(1-hydroxyhexyl)phenyl]-2,2-dimethylpropanamide (18.5 g, 62.6 mmol) in CH2Cl2 (300 mL) was treated with 4-methylmorpholine N-oxide (7.35 g, 62.6 mmol) followed by tetrapropylammonium perruthenate (TPAP, 0.22 g, 0.63 mmol). The mixture was stirred at room temperature for 30 minutes, then treated with additional TPAP (0.88 g, 2.5 mmol) and stirred an additional 30 minutes at room temperature. The mixture was filtered through a pad of MgSO4 atop a pad of silica gel, washing through with EtOAc (500 mL). The filtrate was evaporated under vacuum to afford N-(2-fluoro-4-hexanoylphenyl)-2,2-dimethylpropanamide (17.8 g, 97%) as a white solid.

Workup

  1. stirringstirred an additional 30 minutes at room temperature
  2. filtrationThe mixture was filtered through a pad of MgSO4 atop a pad of silica gel
  3. washwashing through with EtOAc (500 mL)
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-e1f700ec0ab54dd4b23fdb795f963413
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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