Sodium periodate → HCID 16743592, compound

HRID 500650Notes

Reaction equation

HRID 500650 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][C:14](CO)([OH:16])[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:13][C:14](=[O:16])[CH2:15]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 576810553-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-(hydroxymethyl)cyclobutanol

Product 1

HCID 16743592HCID 16743592, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 283E (3.60 g, 9.5 mmol) in THF (100 mL) and water (25 mL) was cooled to 0° C. in an ice bath and treated with sodium periodate (2.42 g, 11.3 mmol). The ice bath was removed, and the mixture stirred for 3.5 h. The mixture was diluted with EtOAc (200 mL), washed with brine (3×), then dried (MgSO4). Solvent removal and drying under vacuum provided the product as a tan solid (2.68 g).

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with EtOAc (200 mL)
  3. washwashed with brine (3×)
  4. dry with materialdried (MgSO4)
  5. customSolvent removal
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-98ca976bac76484da54f02fa850ba732
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

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