Dimethylalumanylium chloride → 5-(6-Chloro-2-hexyl-indol-1-yl)-3-(S)-methyl-5-oxo-pentanoic acid (tert-butyl-diphenyl-silanyl)-methyl ester

HRID 2406665Notes

Reaction equation

HRID 2406665 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C)[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[Cl-:18].C[Al+]C.[C:22]([Si:26]([CH2:39][O:40][C:41](=[O:49])[CH2:42][C@@H:43]([CH3:48])[CH2:44][C:45](Cl)=[O:46])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[C:22]([Si:26]([CH2:39][O:40][C:41](=[O:49])[CH2:42][C@@H:43]([CH3:48])[CH2:44][C:45]([N:7]1[C:8]2[C:4](=[CH:3][CH:2]=[C:10]([Cl:18])[CH:9]=2)[CH:5]=[C:6]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:46])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:24])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 16686359Dimethylalumanylium chlorideHCID 666441725-Chloro-2-hexyl-1-methyl-1H-indoleHCID 866652604-chlorocarbonyl-3-(R)-methyl-butyric acid (tert-butyl-diphenyl-silanyl)-methyl ester

Product 1

HCID 666441375-(6-Chloro-2-hexyl-indol-1-yl)-3-(S)-methyl-5-oxo-pentanoic acid (tert-butyl-diphenyl-silanyl)-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-chloro-2-hexyl-1-methyl-1H-indole in methylene chloride was added dimethyl aluminum chloride at 0 0 C and was stirred for 60 minutes. Then to this mixture, 4-chlorocarbonyl-3-(R)-methyl-butyric acid (tert-butyl-diphenyl-silanyl)-methyl ester was added and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-b1c0abd4039f4229a8120d64977fc0a5
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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