Abecarnil → 6-Hydroxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

HRID 36331Notes

Reaction equation

HRID 36331 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23]CC1C=CC=CC=1)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([OH:23])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 65914AbecarnilHCID 178418361HCID 178418361, compound

Product 1

HCID 153632686-Hydroxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At room temperature and under normal pressure, 7 g (18 mmol) of 6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is hydrogenated in 600 ml of ethanol with 7 g of palladium/carbon (10%) as well as hydrogen for 8.5 hours. After the mixture has been removed from the catalyst by filtration, it is concentrated, thus obtaining 4.8 g (90% yield) of 6-hydroxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester which is further reacted without any additional purification.

Workup

  1. customAt room temperature
  2. customfor 8.5 hours
  3. customAfter the mixture has been removed from the catalyst by filtration, it
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-48e76857ab54483eb2c943cdca1dd1ad
Source dataset
uspto-grants-1995_05
Patent number
US05414002

Reaction notes

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