Methyl iodide → HCID 131727759, compound

HRID 1435938Notes

Reaction equation

HRID 1435938 reaction equation
[CH3:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C@@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:26]>CN(C=O)C.C1COCC1.[Cl-].[Na+].O>[CH3:26][N:10]1[C:11]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[C@H:7]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C@H:8]2[C:9]1=[O:12]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131727758HCID 131727758, compound

Product 1

HCID 131727759HCID 131727759, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (±)-cis tert-butyl 6-methyl-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate (0.5 g, 1.66 mmol) in 10 mL of DMF and 5 mL of THF was added sodium hydride (0.2 g, 60% dispersion in mineral oil, 5.0 mmol). The mixture was allowed to stir at ambient temperature for 1 h and then there was added iodomethane (0.25 mL, 4.0 mmol). The reaction was allowed to stir at ambient temperature for 18 h. The reaction mixture was poured into brine and extracted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.47 g (90%) of (±)-cis tert-butyl 5,6-dimethyl-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate.

Workup

  1. stirringto stir at ambient temperature for 18 h
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ef6d3ffd864640cd915d4f9735966951
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

Loading…