Methyl morpholine oxide → HCID 58307569, compound

HRID 1516451Notes

Reaction equation

HRID 1516451 reaction equation
C[N+]1([O-])CC[O:5]CC1.C([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([F:21])[C:13]=1[OH:22])C=C.[CH3:23][C:24]([CH3:26])=[O:25].O>O=[Os](=O)(=O)=O>[F:21][C:14]1[C:13]([OH:22])=[C:12]([CH2:23][CH:24]([OH:25])[CH2:26][OH:5])[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 58307567HCID 58307567, compound

Product 1

HCID 58307569HCID 58307569, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

N-methylmorpholine N-oxide (2.7 g, 23 mmol) was added to a suspension of Compound 3 (4.55 g, 23 mmol) in 50 mL of acetone/water (10:1) at 0° C. After 7 min OsO4 (1.048 mL, 0.092 mmol) was added slowly. The solution was stirred 36 h at room temperature, and then the solvent was evaporated in vacuo. It was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The filtrate was concentrated to yield the corresponding compound 4 (5.1 g, yield 85.2%).

Workup

  1. customthe solvent was evaporated in vacuo
  2. extractionextracted with ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-afd6dac321334d8d9846a591693f2c1f
Source dataset
uspto-grants-2012_07
Patent number
US08227501B2

Reaction notes

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