Sodium Dithionite → HCID 86668031, compound

HRID 538321Notes

Reaction equation

HRID 538321 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[C:5]([F:11])=[CH:4][CH:3]=1.[OH2:12].C[N+]1([O-])CC[O:17]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:17])([CH3:10])[CH2:9][OH:12])[C:5]([F:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 86668030HCID 86668030, compound

Product 1

HCID 86668031HCID 86668031, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 6-bromo-3-fluoro-2-isopropenyl-pyridine (17.35 g, 80 mmol) in acetone (45 ml) and water (90 ml) was added N-methylmorpholine-N-oxide hydrate (11.4 g, 84 mmol) and osmium tetroxide (5.04 ml, 0.402 mmol). The resulting reaction mixture was stirred at room temperature for 44 hours. Sodium dithionite (2 g) in water (70 ml) was added and the reaction mixture was stirred for 15 minutes and was then filtered and concentrated in vacuo. Ethyl acetate was added and the organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. 18.29 g slightly yellow solid (91% yield). LCMS RtH5=0.64 min (ES+250, 252); 1H-NMR (360 MHz, CDCl3): 7.46 (dd, 1H), 7.35 (dd, 1H), 5.09 (s, 1H, OH), 3.96 (d, 1H), 3.78 (d, 1H), 2.45 (broad, 1H, OH), 1.53 (s, 3H, CH3).

Workup

  1. customThe resulting reaction mixture
  2. stirringthe reaction mixture was stirred for 15 minutes
  3. filtrationwas then filtered
  4. concentrationconcentrated in vacuo
  5. additionEthyl acetate was added
  6. washthe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0f37574a527a421aa7f24a8fe88c0b5e
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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