Aluminium lithium hydride → {2-[5-(1,1-Dimethyl-2-oxo-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

HRID 1274401Notes

Reaction equation

HRID 1274401 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([C:22](=[O:27])NCOC)([CH3:21])[CH3:20])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([CH3:20])([CH3:21])[CH:22]=[O:27])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56977920(2-{2-(3,5-Dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester

Product 1

HCID 54043798{2-[5-(1,1-Dimethyl-2-oxo-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl esterYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-{2-(3,5-dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester (296 mg in 5 mL dry tetrahydrofuran) at 0° C. was added 1.8 mL of a 1M lithium aluminum hydride solution in tetrahydrofuran and the mixture stirred at low temperature. After 1 hour, the reaction was quenched by the careful addition of 0.3M aqueous sodium bisulfate solution. The resulting mixture was extracted with ethyl acetate and the organic portion washed successively with 0.3M aqueous sodium bisulfate, water and brine. This was then dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15) to give the title compound (253 mg).

Workup

  1. customthe reaction was quenched by the careful addition of 0.3M aqueous sodium bisulfate solution
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe organic portion washed successively with 0.3M aqueous sodium bisulfate, water and brine
  4. dry with materialThis was then dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15)

Sources & evidence

ORD record
ord-4480547160b840b4afe681c0e6c7bdef
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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