p-Toluenesulfonic acid monohydrate → HCID 67086833, compound

HRID 2281640Notes

Reaction equation

HRID 2281640 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][O:16]C3CCCCO3)[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][OH:16])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67086824HCID 67086824, compound

Product 1

HCID 67086833HCID 67086833, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-(Tetrahydro-pyran-2-yloxy)-ethyl]-1H-indole-4-carboxylic acid methyl ester (120 mg, 0.396 mmol) in MeOH (10 ml) is added p-toluenesulfonic acid monohydrate (7.25 mg, 0.04 mmol). The reaction is stirred at room temperature for 16 hours and the solvent is removed in vacuo. The residue is dissolved in MeOH (3 ml) and loaded onto a 1 g PEAX cartridge washed with MeOH (20 ml). The filtrate is concentrated in vacuo to give 1-(2-Hydroxy-ethyl)-1H-indole-4-carboxylic acid methyl ester; [M+H]+ 220

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in MeOH (3 ml)
  3. washwashed with MeOH (20 ml)
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1e26b388f0fb4e52ad5ee5de5f5c57f6
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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