Water → HCID 67126778, compound

HRID 2040346Notes

Reaction equation

HRID 2040346 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[OH2:17].C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:32]>O1CCCC1.O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[CH2:10]([O:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([CH2:1][OH:32])([OH:17])[CH2:3][CH2:4]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962Water3×HCID 24437Sodium SulfiteHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 67126738HCID 67126738, compound

Product 1

HCID 67126778HCID 67126778, compound

Reagents, catalysts & solvents 2

HCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 399A (4.77 g) and 4-methylmorpholine 4-oxide hydrate (3.28 g), in a mixture of tetrahydrofuran (90 mL) and water (13.50 mL) was added potassium dioxidodioxoosmium dihydrate (0.325 g) and the resulting suspension was stirred rapidly 18 hours. Sodium sulfite (12.51 g) and water (90 mL) were added and stirring was continued for 1 hour. The reaction was diluted with water (300 mL) and extracted with ethyl acetate (3×200 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel and eluted with a 50, 100% ethyl acetate in hexane step gradient to provide the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel
  8. washeluted with a 50, 100% ethyl acetate in hexane step gradient

Sources & evidence

ORD record
ord-dc1aa96fdcb04153a7a891e729177966
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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