Ammonium Chloride → Methyl 5-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-3-(R)-methyl-5-oxopentanoate

HRID 2406658Notes

Reaction equation

HRID 2406658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[Cl-].C[Al+]C.Cl[C:23](=[O:32])[CH2:24][C@@H:25]([CH3:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28].[Cl-].[NH4+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:30][O:29][C:27](=[O:28])[CH2:26][C@H:25]([CH3:31])[CH2:24][C:23]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[N:7]([CH3:11])[C:6]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:32]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 16686359Dimethylalumanylium chlorideHCID 666441725-Chloro-2-hexyl-1-methyl-1H-indoleHCID 86665257(S)-methyl 5-chloro-3-methyl-5-oxopentanoate

Product 1

HCID 66644148Methyl 5-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-3-(R)-methyl-5-oxopentanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the cold solution of 5-Chloro-2-hexyl-1-methyl-1H-indole in methylene chloride was added dimethyl aluminum chloride solution and was stirred for 30 minutes. Then (S)-methyl 5-chloro-3-methyl-5-oxopentanoate in methylene chloride was added to the reaction mixture and was stirred for 3 hours. The reaction mixture was then treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringwas stirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-7fb67a7849e5422eacd82a9c22555360
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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