Water → N-methanesulfonyl-6-hydroxymethylindole

HRID 1106775Notes

Reaction equation

HRID 1106775 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](OC)=[O:21])[CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9].O.[OH-].[Na+]>C1COCC1>[CH3:7][S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][OH:21])[CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18789637n-Methanesufonyl-6-carbomethoxyindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 18789614N-methanesulfonyl-6-hydroxymethylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (1 M) in THF (2.57 mmol, 2.57 ml) was added dropwise to a 0° C. solution of N-methanesufonyl-6-carbomethoxyindole in dry THF (10 mL, from above). After 30 min, 0.5 ml of water was added dropwise followed by the addition of 0.5 ml 1.0 M NaOH solution. Celite was added and the mixture was filtered through a coarse fritted funnel. The solids were washed with 20 ml ethyl acetate. The filtrate was concentrated under vacuum. The product was purified by flash column chromatography (silica gel, applied to column with toluene, gradient elution 20-50% ethyl acetate/hexane) to give 370 mg of N-methanesulfonyl-6-hydroxymethylindole, a white solid (80% yield).

Workup

  1. additionCelite was added
  2. filtrationthe mixture was filtered through a coarse fritted funnel
  3. washThe solids were washed with 20 ml ethyl acetate
  4. concentrationThe filtrate was concentrated under vacuum
  5. customThe product was purified by flash column chromatography (silica gel, applied to column with toluene, gradient elution 20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fa441be59dea439f96bbe244d8561ac4
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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