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

HRID 2226922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226922
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 542643981,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl esterAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-89cf63e86d344a30b5e738b8c49acb28
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05350762

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