Methyl morpholine oxide → HCID 15557311, compound

HRID 1597436Notes

Reaction equation

HRID 1597436 reaction equation
C=C1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.C[N+]1([O-])CC[O:17][CH2:16]C1.[C:21]([O-:24])(O)=O.[Na+]>C(O)(C)(C)C.O.CC(C)=O.O=[Os](=O)(=O)=O>[OH:17][CH2:16][C:21]1([OH:24])[CH2:3][O:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[O:7][CH2:8]1

Participants

8

Reactant 3

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 5954503-Methylene-3,4-dihydro-2H-1,5-benzodioxepin

Product 1

HCID 15557311HCID 15557311, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A cloudy solution of Example 280A (0.81 g, 5 mmol), 4-methylmorpholine N-oxide (644 mg, 5.5 mmol) in t-butanol (0.4 mL), water (2.5 mL) and acetone (1.5 mL) was treated with OsO4 (0.1 mL, 4% aq. solution) then stirred overnight. The reaction mixture was treated with 2 g NaHCO3, concentrated and partitioned between water and EtOAc. The organics were dried (MgSO4), filtered and concentrated to a white solid (740 mg, 75%). MS (ESI): 219 (M+Na)+.

Workup

  1. concentrationconcentrated
  2. custompartitioned between water and EtOAc
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid (740 mg, 75%)

Sources & evidence

ORD record
ord-bcd630c2757549babb9dd36a2d2fa377
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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