Methyl iodide → HCID 131727757, compound

HRID 1435935Notes

Reaction equation

HRID 1435935 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:14]2[NH:13][C:12](=[O:15])[C@@H:11]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@@H:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1.I[CH3:27]>C1COCC1>[CH3:3][O:4][C:5]1[C:14]2[N:13]([CH3:27])[C:12](=[O:15])[C@@H:11]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@@H:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131727755HCID 131727755, compound

Product 1

HCID 131727757HCID 131727757, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60 mg of 60% dispersion in mineral oil, hexane-washed, 1.5 mmol) in 5 mL of THF was added (±)-cis tert-butyl 6-methoxy-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate from Example 10, Part A (0.40 g, 1.25 mmol) in 4 mL of THF. The reaction was stirred at ambient temperature for 1 h, at which time gas evolution had ceased. Then there was added iodomethane (0.23 mL, 3.75 mmol) and the resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was quenched with 1N HCl and was extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated in vacuo to afford 0.38 g (91%) of the title compound which was used without purification.

Workup

  1. stirringto stir at ambient temperature for 18 h
  2. customThe reaction was quenched with 1N HCl
  3. extractionwas extracted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ec4dd83efa947d99059f02d72cd8c7f
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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