Water → HCID 59129524, compound

HRID 1964326Notes

Reaction equation

HRID 1964326 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=2)([CH3:14])[C:9](OCC)=[O:10].O.[OH-].[Na+]>C1COCC1>[CH3:14][C:8]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=2)([CH3:7])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59129201HCID 59129201, compound

Product 1

HCID 59129524HCID 59129524, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of LiAlH4 (1.0 M in THF, 1.1 mL, 1.1 mmol) in THF (5 mL) at 0° C. was added a solution of ethyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (0.20 g, 0.72 mmol) in THF (3.4 mL) dropwise. After addition, the mixture was allowed to warm up to room temperature and was stirred for 3 h. The mixture was cooled to 0° C. before water (2 mL) was slowly added followed by careful addition of 15% NaOH (2 mL) and water (4 mL). The mixture was stirred at room temperature for 0.5 h and was filtered through a short plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propan-1-ol (0.098 g, 58%).

Workup

  1. additionAfter addition
  2. additionwas slowly added
  3. stirringThe mixture was stirred at room temperature for 0.5 h
  4. filtrationwas filtered through a short plug of celite
  5. customThe organic layer was separated from the aqueous layer
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-631af3f7e82e424d8b408c60435bf9cd
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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