Methyl morpholine oxide → 7-Chloro-6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehyde

HRID 577969Notes

Reaction equation

HRID 577969 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([CH3:11])[C:6]=2[CH:5]=[C:4]([CH2:12][OH:13])[C:3]=1[N:14]1[CH2:19][C@H:18]([CH3:20])[O:17][C@H:16]([CH3:21])[CH2:15]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([CH3:11])[C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[C:3]=1[N:14]1[CH2:15][C@H:16]([CH3:21])[O:17][C@H:18]([CH3:20])[CH2:19]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67356497{7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazol-5-yl}methanol2×

Product 1

HCID 873697927-Chloro-6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of {7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazol-5-yl}methanol (Intermediate 372, 130 mg, 4.4 mmol) in anhydrous DCM (5 mL), was added NMO (103 mg, 8.8 mmol) and TPAP (31 mg, 0.88 mmol) at 0° C. and allowed to stir for 1 h at room temperature. The reaction mixture was filtered and the solvents were removed under vacuum and the residue was purified over silica gel chromatography column using ethylacetate-pet. ether gradient to give solid. Yield: 35 mg, (27%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed under vacuum
  3. customthe residue was purified over silica gel chromatography column
  4. customto give solid

Sources & evidence

ORD record
ord-8e789bd784014d8ba414c27770af170c
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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