Sodium Dithionite → HCID 10420440, compound

HRID 1987676Notes

Reaction equation

HRID 1987676 reaction equation
[CH3:1][C:2]1([CH3:12])O[CH:6]2C=CC[O:11][CH:5]2[CH2:4][O:3]1.C[N+]1([O-])CC[O:17]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[O-][Si]([O-])=O.[Mg+2].C1COCC1.[C:39]([OH:43])([CH3:42])([CH3:41])C.[OH2:44]>O=[Os](=O)(=O)=O.O>[CH3:1][C:2]1([CH3:12])[O:3][CH:4]2[CH:41]([OH:17])[CH:39]([OH:43])[CH2:42][O:11][CH:5]2[CH2:6][O:44]1

Participants

8

Reactant 5

HCID 24489Sodium DithioniteHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 57723926HCID 57723926, compound

Product 1

HCID 10420440HCID 10420440, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (50 mg, 0.29 mmol) in 4.5 mL of THF-tert-BuOH—H2O (1:3:0.5) was added NMO (45 mg, 0.32 mmol) and the solution was stirred for 5 min at ambient temperature. OsO4 (15 μL, 25 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 4 days. Sodium hydrosulphite (0.2 g), Florisil (2.0 g) and H2O (5 ml) were added and the mixture was stirred for 30 minutes, wash with acetone (100 mL), filtered through filter paper and extracted with EtOAc (80 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo, and the residue was purified by flash chromatography with 60% EtOAc-hexane.

Workup

  1. stirringthe solution was stirred at ambient temperature for 4 days
  2. stirringthe mixture was stirred for 30 minutes
  3. washwash with acetone (100 mL)
  4. filtrationfiltered
  5. filtrationthrough filter paper
  6. extractionextracted with EtOAc (80 mL×2)
  7. washThe combined organic layers were washed with brine (50 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customthe residue was purified by flash chromatography with 60% EtOAc-hexane

Sources & evidence

ORD record
ord-0d198a8abbd54daca5e41a0d49dce57f
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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