Phenethyl bromide → (3aS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-phenylethyl)-3a,8-dimethylpyrrolo[2,3-b]indole

HRID 414181Notes

Reaction equation

HRID 414181 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]1[NH:13][CH2:14][CH2:15][C:6]21[CH3:16].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C@H:7]1[N:13]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:15][C@@:6]21[CH3:16]

Participants

3

Reactant 2

HCID 7666Phenethyl bromideHCID 612787HCID 612787, compound

Product 1

HCID 57011492(3aS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-phenylethyl)-3a,8-dimethylpyrrolo[2,3-b]indole

Procedure

A stirred mixture, under nitrogen, of 8.73 g of 1,2,3,3a,8,8a-hexahydro-5-methoxy-3a,8-dimethylpyrrolo[2,3-b]indole, 9.25 g of 2-(bromoethyl)benzene and 8.29 g of milled, anhydrous potassium carbonate in 75 ml of degassed, dry dimethylformamide is heated at 70°-75° for 8 hours and thereafter stirred at room temperature overnight. The reaction mixture is decanted into 1.5 liters of water and the product is extracted into ethyl acetate (2×250 ml). The combined organic extracts are washed twice with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue is subjected to flash chromatography over silica gel using methanol/ethyl acetate mixtures as eluent. The fractions containing the product are combined and concentrated to afford pure (3aS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-phenylethyl)-3a,8-dimethylpyrrolo[2,3-b]indole.

Workup

  1. customanhydrous potassium carbonate in 75 ml of degassed
  2. temperaturedry dimethylformamide is heated at 70°-75° for 8 hours
  3. customThe reaction mixture is decanted into 1.5 liters of water
  4. extractionthe product is extracted into ethyl acetate (2×250 ml)
  5. washThe combined organic extracts are washed twice with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionThe fractions containing the product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7eda3160497f4320b8217c2430ac4e48
Source dataset
uspto-grants-1988_12
Patent number
US04791107

Reaction notes

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