Ammonium Chloride → 5-(3-Hexyl-1-methyl-1H-indol-2-yl)-5-oxo-pentanoic acid methyl ester

HRID 2406636Notes

Reaction equation

HRID 2406636 reaction equation
[CH2:1]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].C[Al+]C.[CH3:21][O:22][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].[Cl-].[NH4+]>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:21][O:22][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][C:27]([C:8]1[N:9]([CH3:16])[C:10]2[C:15]([C:7]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:28]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 73916Methyl 4-chloroformylbutyrateHCID 16686359Dimethylalumanylium chlorideHCID 687471243-Hexyl-1-methyl-1H-indole

Product 1

HCID 666439815-(3-Hexyl-1-methyl-1H-indol-2-yl)-5-oxo-pentanoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hexyl-1-methyl-1H-indole in methylene chloride at 0° C. was added dimethyl aluminum chloride solution in hexane. The reaction mixture was stirred for 30 minutes. To this solution 4-chlorocarbonyl-butyric acid methyl ester was added at 0 ° C. and the reaction mixture was stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e0101db256244d689f75f1f6c5c01c60
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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