Methyl morpholine oxide → 2-Benzyl-2-azabicyclo[2.2.2]octan-6-one

HRID 1987239Notes

Reaction equation

HRID 1987239 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[C@@H:10]([OH:16])[CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:16])[CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 2802928(6S)-2-Benzyl-2-azabicyclo[2.2.2]octan-6-OL

Product 1

HCID 123174732-Benzyl-2-azabicyclo[2.2.2]octan-6-oneYield 81%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirring suspension of (6S)—N-benzyl-2-azabicyclo[2.2.2]octan-6-ol (1.5 g, 6.9 mmol, Maybridge) and activated 4 Å MS (1.0 g) in acetonitrile (70 mL) at 23° C. was sequentially added 4-methylmorpholine-N-oxide (1.2 g, 10 mmol) and tetrapropylammonium perruthenate (240 mg, 0.69 mmol). After stirring the resulting black suspension for 30 min, the mixture was concentrated in vacuo, and the resulting residue was purified by flash chromatography (20-50% ethyl acetate in hexanes) to provide N-benzyl-2-azabicyclo[2.2.2]octan-6-one as an orange oil (1.2 g, 81%). MS (AP CI) 216 (M+H).

Workup

  1. stirringAfter stirring the resulting black suspension for 30 min
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe resulting residue was purified by flash chromatography (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-423c56243d684bc58f31636106fb79c9
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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