Methyl morpholine oxide → HCID 23147977, compound

HRID 2249879Notes

Reaction equation

HRID 2249879 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-339fb29482e94a8f8d6eafc343f2014a
Source dataset
uspto-grants-2008_01
Patent number
US07314936B2

Reaction notes

Loading…