p-Toluenesulfonic acid → 6-(2-Ethoxytetrahydrofuran-4-yl)-4-methyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 1731751Notes

Reaction equation

HRID 1731751 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([CH:20]1[CH2:24][O:23][CH:22]([OH:25])[CH2:21]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2].[C:26]1(C)C=CC(S(O)(=O)=O)=C[CH:27]=1.C(OCC)(OCC)OCC>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([CH:20]1[CH2:24][O:23][CH:22]([O:25][CH2:26][CH3:27])[CH2:21]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 13505217HCID 13505217, compound

Product 1

HCID 538306546-(2-Ethoxytetrahydrofuran-4-yl)-4-methyl-beta-carboline-3-carboxylic acid ethyl esterYield 135.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

100 mg (0.29 mmol) of 6-(2-hydroxytetrahydrofuran-4-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester is refluxed in 5 ml of toluene with 10 mg of p-toluenesulfonic acid and 52 mg (0.35 mmol) of triethyl orthoformate for 1.5 hours. After concentration, the mixture is chromatographed over silica gel with toluene:glacial acetic acid:water=10:10:1 thus obtaining 29 mg (27% of theory) of 6-(2-ethoxytetrahydrofuran-4-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester as an oil.

Workup

  1. concentrationAfter concentration
  2. customthe mixture is chromatographed over silica gel with toluene

Sources & evidence

ORD record
ord-e3c5602ad7d94a1fb72b1de796a40546
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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