Methyl morpholine oxide → 3-Benzyl-3-azabicyclo[3.2.1]octan-6-one

HRID 272615Notes

Reaction equation

HRID 272615 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][CH:12]2[OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][C:12]2=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 598378273-Benzyl-3-azabicyclo[3.2.1]octan-6-ol

Product 1

HCID 598378303-Benzyl-3-azabicyclo[3.2.1]octan-6-oneYield 96.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-benzyl-3-aza-bicyclo[3.2.1]octan-6-ol (8 mmol) in anhydrous dichloromethane at 0° C. under nitrogen was treated with of N-methyl morpholine N-oxide (12 mmol), 1 weight equivalent of oven dried 4 angstrom sieves and TPAP (tetrapropylammonium perruthenate) (0.2 mmol). The reaction mixture was stirred for 30 min. at 0° C. then allowed to warm to room temperature with stirring for an additional 1 h. The reaction was filtered through a plug of silica gel and eluted with ethyl acetate then striped to an oil. Purification by silica gel chromatography eluted with 15% ethyl acetate/hexanes produced an oil (7.7 mmol). APCl MS m/z 216.2 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringwith stirring for an additional 1 h
  3. filtrationThe reaction was filtered through a plug of silica gel
  4. washeluted with ethyl acetate
  5. customPurification by silica gel chromatography
  6. washeluted with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-19b8d37fdb01461e9888f68e2f407a5e
Source dataset
uspto-grants-2008_11
Patent number
US07456177B2

Reaction notes

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