Sodium Sulfite → HCID 86624796, compound

HRID 494100Notes

Reaction equation

HRID 494100 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([CH:21]=C)[N:12]2[CH:17]([CH3:18])[CH2:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:29].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([CH:21]=[O:29])[N:12]2[CH:17]([CH3:18])[CH2:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 68865230HCID 68865230, compound

Product 1

HCID 86624796HCID 86624796, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 8-(benzyloxy)-2,4-dimethyl-1-oxo-6-vinyl-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (0.11 g, 0.29 mmol), osmium tetroxide (2.5% in t-butanol, 0.59 mL, 0.058 mmol), sodium periodate (0.19 g, 0.87 mmol) in aqueous THF (6 mL, 1:2 v/v) was stirred at room temperature for 4 hours. The reaction mixture was treated with 10% aqueous sodium sulfite and diluted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with a hexanes and ethyl acetate gradient to provide the titled product.

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. washeluted with a hexanes and ethyl acetate gradient

Sources & evidence

ORD record
ord-8219a255626a4126a113e55f0e1377c8
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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