Water → HCID 53735277, compound

HRID 2226919Notes

Reaction equation

HRID 2226919 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:19][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:19][C:9]2[N:10]([CH3:22])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53857755HCID 53857755, compound

Product 1

HCID 53735277HCID 53735277, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydro-7-methoxycyclopent[b]indole-2-carboxylic acid ethyl ester (10 g, 0.04 mole) in 75 ml of dimethylformamide, was added sodium hydride (1.7 g, 60% in oil, 0.043 mole). After stirring at ambient temperature for two hours, a solution of methyl iodide (2.7 ml, 0.043 mole) in dimethylformamide (10 ml) was added, and the mixture was stirred at 70° C. for five hours. After cooling, the mixture was poured into 200 ml of water, stirred for five minutes, and extracted with ethyl acetate. The organic layer was washed successively with water (2×) and a saturated NaCl solution, and then dried over anhydrous MgSO4. After filtering, the solvent was evaporated to afford a dark oil (~10 g) which was eluted on a silica gel column with dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick yellow oil, 6.8 g.

Workup

  1. stirringthe mixture was stirred at 70° C. for five hours
  2. temperatureAfter cooling
  3. stirringstirred for five minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with water (2×)
  6. dry with materiala saturated NaCl solution, and then dried over anhydrous MgSO4
  7. filtrationAfter filtering
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7dd2c50d2c434978ab11d0eef6fd88d3
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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