Sodium periodate → HCID 58042797, compound

HRID 564193Notes

Reaction equation

HRID 564193 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:20][CH:19]=2)=C)[C:11](=[O:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:32].[Na+]>C(#N)C.O.S([O-])([O-])(=O)=S.[Na+].[Na+].O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16](=[O:32])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:20][CH:19]=2)[C:11](=[O:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 58042760HCID 58042760, compound

Product 1

HCID 58042797HCID 58042797, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To 200 mg (0.50 mmol) 4-benzyloxy-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-allyl]-1H-pyridin-2-one (example 26.1) in 6.0 mL acetonitrile is added at RT subsequently a solution of 4 mg (0.02 mmol) ruthenium(III)-trichloride hydrate in 1.0 mL water and then 214 mg (1.00 mmol) sodium metaperiodate in small portions. The reaction mixture is stirred 4 h at RT and is diluted with aqueous 10% sodium thiosulfate solution. The layers are separated and the aqueous phase is extracted with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters xbridge; water (15% NH4OH)/acetonitrile (15% NH4OH) 95:5 to 5:95).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with DCM
  3. dry with materialThe combined organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is purified via reverse HPLC chromatography (Waters xbridge; water (15% NH4OH)/acetonitrile (15% NH4OH) 95:5 to 5:95)

Sources & evidence

ORD record
ord-8484a18d08854c3181b8965a172c24cd
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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