Sodium borohydride → Methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate

HRID 1015440Notes

Reaction equation

HRID 1015440 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19606277Methyl 3-formyl-1H-indole-5-carboxylate

Product 1

HCID 67300394Methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 350 mg portion of methyl 3-formyl-1H-indole-5-carboxylate was suspended in 10 ml of methanol, and 90 mg of sodium borohydride was added at 0° C., followed by stirring at room temperature for 30 minutes. After evaporation of the solvent, ethyl acetate and water were added thereto, and the ethyl acetate layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent under a reduced pressure, 337 mg of methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate was obtained as a colorless solid.

Workup

  1. customAfter evaporation of the solvent, ethyl acetate and water
  2. additionwere added
  3. washthe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-9d535cbbc5b74063ab78b1c1f7dddad2
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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