ZK 91296 → HCID 178470225, compound

HRID 329961Notes

Reaction equation

HRID 329961 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[CH2:19][O:20][CH3:21])=[C:15]([O:22]CC1C=CC=CC=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]>C(O)C.[Ni]>[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[CH2:19][O:20][CH3:21])=[C:15]([OH:22])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 123700ZK 91296

Product 1

HCID 178470225HCID 178470225, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

10 g of 5-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is refluxed for 3 hours in 100 ml of ethanol with 4 g of Raney nickel. After the catalyst has been removed by filtration, the filtrate is concentrated under vacuum. The residue is chromatographed over silica gel with methylene chloride+ethanol/1000+75, thus obtaining 7.2 g of 5-hydroxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, mp 179°-181° C.

Workup

  1. customAfter the catalyst has been removed by filtration
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe residue is chromatographed over silica gel with methylene chloride+ethanol/1000+75

Sources & evidence

ORD record
ord-a888ea2cff7444eb89c3a36bb0daf8ac
Source dataset
uspto-grants-1990_01
Patent number
US04894377

Reaction notes

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