Methyl morpholine oxide → HCID 23147977, compound

HRID 2361867Notes

Reaction equation

HRID 2361867 reaction equation
[CH2:1]([N:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][CH:5]([OH:9])[CH2:6][O:7][CH3:8])[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.C([O-])(O)=O.[Na+].CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([N:3]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:4][C:5](=[O:9])[CH2:6][O:7][CH3:8])[CH3:2]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 21312729HCID 21312729, compound

Product 1

HCID 23147977HCID 23147977, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-(ethyl-phenyl-amino)-3-methoxy-propan-2-ol (1.95 g, 9.32 mmol) and NMO (2.18 g, 2.0 eq.) in dichloromethane (15 mL) was treated with TPAP (150 mg, 0.05 eq.) at room temperature until reaction was completed. The reaction mixture was diluted with sat. NaHCO3 (50 mL) and extracted with 3×30 mL EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated and the product was purified by chromatography (10 to 15% EtOAc-hexanes) to give 1-(ethyl-phenyl-amino)-3-methoxy-propan-2-one (0.98 mg, 51%).

Workup

  1. extractionextracted with 3×30 mL EtOAc
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe product was purified by chromatography (10 to 15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-2b9504b75bb34de4a64b03f7c424b311
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

Loading…