Methyl iodide → HCID 69056562, compound

HRID 2100568Notes

Reaction equation

HRID 2100568 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:13]2[C:12]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:10]=[CH:9][C:8]=2[C@H:7]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][C@H:6]2[NH:5]1.I[CH3:29]>C1COCC1>[CH3:29][N:5]1[C@@H:6]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][C@@H:7]2[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([C:14]([F:16])([F:17])[F:15])[C:13]=2[C:4]1=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69056519HCID 69056519, compound

Product 1

HCID 69056562HCID 69056562, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (17 mg of 60% in mineral oil, hexane-washed, 0.42 mmol) in 2 mL of THF at ambient temperature was added (±)-cis-tert-butyl 5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 1, Part H (75 mg, 0.21 mmol) as a solution in 2 mL of THF. The reaction was stirred for 20 min, at which time gas evolution had ceased and the reaction mixture was homogeneous. Then there was added iodomethane (0.039 mL, 0.63 mmol) and the reaction was allowed to stir at ambient temperature for 1 h. The reaction was quenched with water, diluted with EtOAc and washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 2:1 hexane/EtOAc) to afford 30 mg (39%) of the title compound. LRMS (ESI): 315.22 (M+H—C4H8)+.

Workup

  1. stirringto stir at ambient temperature for 1 h
  2. customThe reaction was quenched with water
  3. additiondiluted with EtOAc
  4. washwashed with 1N HCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (230-400 mesh silica gel, elution with 2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-903f2772c5bc4aab9f1bbe2d55844eda
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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