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

HRID 16211Notes

Reaction equation

HRID 16211 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-15ceb4157b1d41a3b0c06c610f11091f
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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