Methyl iodide → HCID 86612120, compound

HRID 494116Notes

Reaction equation

HRID 494116 reaction equation
[CH2:1]([N:3]1[CH2:8][C@H:7]([CH3:9])[N:6]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([OH:13])=[C:5]2[C:4]1=[O:19])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH2:1]([N:3]1[CH2:8][C@H:7]([CH3:9])[N:6]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([O:13][CH3:20])=[C:5]2[C:4]1=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86624797HCID 86624797, compound

Product 1

HCID 86612120HCID 86612120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl (4S)-2-ethyl-8-hydroxy-4-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-carboxylate (6.6 g, 24.8 mmol), anhydrous potassium carbonate (13.7 g, 99.1 mmol, 325 mesh), and iodomethane (4.2 g, 29.7 mmol) in anhydrous DMF (123 mL) was stirred at room temperature overnight. The mixture was filtered and concentrated under vacuum. The residue was partitioned between chloroform and dilute hydrochloric acid. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a gradient of 0-3% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound. Residual methanol was removed by concentrating from its solution in toluene under vacuum.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between chloroform and dilute hydrochloric acid
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-05d33f3d6a144b3195196ba319d67e15
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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