HCID 178418361, compound → HCID 13799208, compound

HRID 1722255Notes

Reaction equation

HRID 1722255 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]([OH:22])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[H][H]>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[CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]=3[C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178470225HCID 178470225, compound

Product 1

HCID 13799208HCID 13799208, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.7 g of 5-hydroxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester is hydrogenated in 50 ml of ethanol with 0.5 g of Raney nickel at a hydrogen pressure of 80 bars and a temperature of 100° C. for 6 hours. After filtering off of the catalyst, the solvent is evaporated in a vacuum. The residue is chromatographed on silica gel with dichloromethane and ethanol=10+1. 0.108 g of 4-methoxymethyl-5-oxo-5,6,7,8-tetrahydro-beta-carboline-3-carboxylic acid ethyl ester with a melting point of 249°-250° C. is obtained.

Workup

  1. filtrationAfter filtering off of the catalyst
  2. customthe solvent is evaporated in a vacuum
  3. customThe residue is chromatographed on silica gel with dichloromethane and ethanol=10+1

Sources & evidence

ORD record
ord-659a2b31dc5f484592d8e53b96a0de57
Source dataset
uspto-grants-1989_08
Patent number
US04855295

Reaction notes

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