Methyl morpholine oxide → HCID 59273060, compound

HRID 906980Notes

Reaction equation

HRID 906980 reaction equation
[OH:1][C@H:2]1[CH2:6][C@@H:5]([CH3:7])[N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:3]1[CH3:18].C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:18][C@H:3]1[C:2](=[O:1])[CH2:6][C@@H:5]([CH3:7])[N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 59273085HCID 59273085, compound

Product 1

HCID 59273060HCID 59273060, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution (20 mL) of benzyl (2S,3S,5R)-3-hydroxy-2,5-dimethylpyrrolidine-1-carboxylate (1.30 g) in acetonitrile were added tetrapropylammonium perruthenate (92 mg), 4-methylmorpholine N-oxide (1.22 g) and molecular sieves 4A powder (1.32 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, the residue was suspended in ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/1) to give the title compound as colorless oil (yield: 1.30 g, yield: 100%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/1)

Sources & evidence

ORD record
ord-b073b27662934ce0bdcfec6aaaee1906
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

Loading…