Water → 5-Bromo-1H-indole-3-ethanol

HRID 1019005Notes

Reaction equation

HRID 1019005 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[C:10]([CH2:18][C:19](OCC)=[O:20])=[CH:9]1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[Br:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[C:10]2[CH2:18][CH2:19][OH:20]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18399760N-tert-butoxycarbonyl-5-bromo-3-ethoxycarbonylmethylindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 1229565-Bromo-1H-indole-3-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6 g of N-tert-butoxycarbonyl-5-bromo-3-ethoxycarbonylmethylindole in 50 ml of tetrahydrofuran is added dropwise to a suspension, cooled to 0° C., of 0.9 g of LiAlH4 in 35 ml of tetrahydrofuran. After stirring for 20 hours at ambient temperature, the mixture is cooled to 0° C. and then treated in succession with 0.9 ml of water, 3.2 ml of an aqueous 20% sodium hydroxide solution and 3.6 ml of water. After filtration and concentration of the filtrate in vacuo, the residue is chromatographed on silica gel (dichloromethane/ethyl acetate: 90/10), enabling the expected product to be isolated.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. filtrationAfter filtration and concentration of the filtrate in vacuo
  3. customthe residue is chromatographed on silica gel (dichloromethane/ethyl acetate: 90/10)
  4. customto be isolated

Sources & evidence

ORD record
ord-b205e65a00a7433ba90a416188af4478
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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