Methyl morpholine oxide → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazole-5-carbaldehyde

HRID 245545Notes

Reaction equation

HRID 245545 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH2:19][OH:20])=[CH:17][C:12]3[C:13]([CH3:16])=[N:14][S:15][C:11]=3[C:10]=2[F:21])[CH2:3]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH:19]=[O:20])=[CH:17][C:12]3[C:13]([CH3:16])=[N:14][S:15][C:11]=3[C:10]=2[F:21])[CH2:3]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67357470{6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazol-5-yl}methanol2×

Product 1

HCID 866581366-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To an ice-cooled solution of {6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazol-5-yl}methanol (Intermediate 157, 0.18 g, 0.6 mmol) in DCM/CH3CN mixture (3 mL, 1:1 v/v) was added NMO (0.12 g, 0.7 mmol) followed TPAP (0.04, 0.2 mmol) and mixture stirred for 2 h at room temperature. The reaction mixture filtered through silica gel bed and washed with EtOAc. The organic phase concentrated under reduced pressure to give title compound as a yellow crystalline solid. Yield: 0.12 g (67%).

Workup

  1. filtrationThe reaction mixture filtered through silica gel bed
  2. washwashed with EtOAc
  3. concentrationThe organic phase concentrated under reduced pressure

Sources & evidence

ORD record
ord-6abea8bba8aa487b83a28dc8dda7ea19
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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