Water → 1,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl ester

HRID 2226922Notes

Reaction equation

HRID 2226922 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8]1[CH2:27][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])[CH3:4].[CH3:28]I.O>CN(C)C=O>[CH2:3]([O:5][C:6]([CH:8]1[CH2:27][C:11]2[N:12]([CH3:28])[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 541882621,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester

Product 1

HCID 542643981,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl esterYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% in oil, 3.0 g, 0.075 mole) in 25 ml of dry dimethylformamide, was added a solution of 1,2,3,4-tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester (23.5 g, 0.07 mole) in 100 ml of dry dimethylformamide. After stirring at ambient temperature for two hours, a solution of methyl iodide (4.7 ml, 0.075 mole) in 20 ml of dimethylformamide was added, and the mixture was stirred at 70° C. for five hours. After cooling, the mixture was poured into 500 ml of water, stirred for five minutes, and then extracted with ethyl acetate (3×). The organic layer was washed successively with water and saturated sodium chloride solution, and dried over anhydrous MgSO4. After filtering, the solvent was evaporated to afford a brown oil (~25 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fraction was concentrated to a thick brown oil, 20.6 g, which solidified on cooling, m.p. 90°-95° C. A sample of this material was recrystallized from ethanol to give the product as an off-white solid, m.p. 109°-110° C.

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 (3×)
  5. washThe organic layer was washed successively with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationAfter filtering
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-89cf63e86d344a30b5e738b8c49acb28
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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