Methyl morpholine oxide → HCID 86658113, compound

HRID 245507Notes

Reaction equation

HRID 245507 reaction equation
[F:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[F:14].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[F:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[F:14]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67356869(6,7-Difluoro-3-methyl-1,2-benzisoxazol-5-yl)methanol2×

Product 1

HCID 86658113HCID 86658113, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of (6,7-difluoro-3-methyl-1,2-benzisoxazol-5-yl)methanol (Intermediate 334, 200 mg, 1.0 mmol) in CH2Cl2 (10 mL) was added NMO (235 mg, 2.0 mmol) followed TPAP (35 mg, 0.1 mmol) and mixture stirred for 2 hours at room temperature. The reaction mixture filtered thorough silica gel bed and washed with EtOAc. The organic phase was concentrated under reduced pressure to give product as a yellow solid. Yield: 150 mg (76%).

Workup

  1. filtrationThe reaction mixture filtered thorough silica gel bed
  2. washwashed with EtOAc
  3. concentrationThe organic phase was concentrated under reduced pressure
  4. customto give product as a yellow solid

Sources & evidence

ORD record
ord-4da751ce47054cc7819e8d53e8067aa0
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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