Methyl morpholine oxide → 5-(Tert-butyldimethylsilyloxy)cyclooctanone

HRID 2115609Notes

Reaction equation

HRID 2115609 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][CH:7]1[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][CH:7]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 143216785-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanol

Product 1

HCID 109780905-(Tert-butyldimethylsilyloxy)cyclooctanone

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrapropylammonium perruthenate (0.82 g, 2.43 mmol) was added to a stirred and cooled (0° C.) solution of Example 5A (12.11 g, 46.90 mmol), 4-methylmorpholine N-oxide (8.24 g, 70.35 mmol), and 4 Å molecular sieves (23 g) in dry dichloromethane (120 mL). After the addition, the mixture was warmed to room temperature and stirred for another three hours. The black mixture was filtered through a pad of Celite and the solvent was evaporated. The residue was purified over silica gel using 5-50% ethyl acetate in hexanes to give the title compound as an oil.

Workup

  1. additionAfter the addition
  2. stirringstirred for another three hours
  3. filtrationThe black mixture was filtered through a pad of Celite
  4. customthe solvent was evaporated
  5. customThe residue was purified over silica gel using 5-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e19eb72e192b4d0e8e86e87185fded2e
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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