HCID 13243481, compound → HCID 13243474, compound

HRID 1762960Notes

Reaction equation

HRID 1762960 reaction equation
C([N:8]([CH2:13][CH:14]([C:16]1[CH:24]=[CH:23][C:22]([O:25]CC2C=CC=CC=2)=[C:21]2[C:17]=1[CH:18]=[C:19]([CH2:33][OH:34])[NH:20]2)[OH:15])[C:9]([CH3:12])([CH3:11])[CH3:10])C1C=CC=CC=1>CO.[C].[Pd]>[C:9]([NH:8][CH2:13][CH:14]([C:16]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]2[C:17]=1[CH:18]=[C:19]([CH2:33][OH:34])[NH:20]2)[OH:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 1

HCID 13243481HCID 13243481, compound

Product 1

HCID 13243474HCID 13243474, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

229 mg of 2-(N-benzyl-N-tert-butylamino)-1-(7-benzyloxy-2-hydroxymethylindol-4-yl)ethanol is hydrogenated in 10 ml of methanol for 10 minutes in the presence of 40 mg of 10% palladium-carbon, filtered, the filtrate concentrated and recrystallized from ethanol/diisopropyl ether, yielding 95 mg of 2-(N-tert-butylamino)-1-(7-hydroxy-2-hydroxymethylindol-4-yl) ethanol, mp 150° C. (decomposition).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. customrecrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-22cfb752ac024da5b94798b0630cf1ee
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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