Sodium periodate → (Z)-butoxyimino-[(2S)-2-carboxypyrrolidin-1-yl]-oxidoazanium

HRID 388213Notes

Reaction equation

HRID 388213 reaction equation
[CH2:1]([O:5]/[N:6]=[N+:7](/[N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][OH:15])\[O-:8])[CH2:2][CH2:3][CH3:4].I([O-])(=O)(=O)=[O:17].[Na+]>CC#N.C(Cl)(Cl)(Cl)Cl.O.O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:5]/[N:6]=[N+:7](/[N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:17])=[O:15])\[O-:8])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 88851203(Z)-butoxyimino-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-oxidoazanium

Product 1

HCID 87274658(Z)-butoxyimino-[(2S)-2-carboxypyrrolidin-1-yl]-oxidoazanium

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 22592919water acetonitrile CCl4Solvent

Procedure

To a solution of {(2S)-1-[(Z)-1-butoxy-NNO-azoxy]pyrrolidin-2-yl}methanol (360 mg, 1.66 mmol) and sodium periodate (1.06 g, 4.97 mmol) in 17.5 mL of CH3CN/CCl4/H2O (2:2:3) was added ruthenium(III) chloride hydrate (34 mg, 1.66 mmol). After stirring at rt over night, the mixture was extracted with CH2Cl2 (3×50 mL), dried over MgSO4 and concentrated to give the title product, which was used directly.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6e0bf8d3fab8420bbc8c5601859ab984
Source dataset
uspto-grants-2013_02
Patent number
US08377911B2

Reaction notes

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