Sodium Iodide → HCID 67423006, compound

HRID 1393005Notes

Reaction equation

HRID 1393005 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]3[C:13]4([CH2:14][CH2:15][C:4]=2[CH:3]=1)[CH:9]([CH2:10][N:11]([C:16](=[O:18])[CH3:17])[CH2:12]4)[CH2:8][CH2:7]3.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[I-].[Na+]>CN(C=O)C>[CH2:27]([O:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]3[C:13]4([CH2:14][CH2:15][C:4]=2[CH:3]=1)[CH:9]([CH2:10][N:11]([C:16](=[O:18])[CH3:17])[CH2:12]4)[CH2:8][CH2:7]3)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 67422783HCID 67422783, compound

Product 1

HCID 67423006HCID 67423006, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Hydroxy-5,6,6a,7,10,11-hexahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrol-8-yl)-ethanone (Example 5B) (10.0 mg, 0.037 mmol) and potassium carbonate (25 mg, 0.18 mmol) were dissolved in DMF (0.5 mL). Benzyl chloride (10.2 μL, 0.088 mmol) and sodium iodide (5 mg) were added. The mixture was stirred at rt for 24 hr, quenched with water (2 mL), and extracted with CH2Cl2 (5 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane, providing 5.5 mg (41.3%) of the title compound.

Workup

  1. customquenched with water (2 mL)
  2. extractionextracted with CH2Cl2 (5 mL×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-214e2db17f494041922711ec9b4ab639
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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