HCID 13067575, compound → HCID 13067590, compound

HRID 638006Notes

Reaction equation

HRID 638006 reaction equation
[ClH:1].C([O:9][C:10]1[CH:19]=[CH:18][C:17]2[C@@H:16]([OH:20])[C@H:15]([NH:21][CH:22]([CH3:31])[CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][CH2:13][C:12]=2[C:11]=1[C:32]([NH2:34])=[O:33])C1C=CC=CC=1>CO.[Pd]>[ClH:1].[OH:9][C:10]1[CH:19]=[CH:18][C:17]2[C@@H:16]([OH:20])[C@H:15]([NH:21][CH:22]([CH3:31])[CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:14][CH2:13][C:12]=2[C:11]=1[C:32]([NH2:34])=[O:33]

Participants

4

Reactant 1

HCID 13067575HCID 13067575, compound

Product 1

HCID 13067590HCID 13067590, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 50 ml of methanol was dissolved 1 g of trans-2-benzyloxy-5-hydroxy-6-(1-methyl-3-phenylpropylamino)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride and catalytic reduction was carried out in the presence of 1 g of 10% palladium-on-carbon at atmospheric temperature and pressure. After the absorption of hydrogen was completed, the catalyst was filtered off and the filtrate was distilled under reduced pressure. To the residue was added 50 ml of ethyl ether, whereby 0.56 g of trans-2,5-dihydroxy-6-(1-methyl-3-phenylpropylamino)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride was obtained as colorless powder.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst was filtered off
  3. distillationthe filtrate was distilled under reduced pressure
  4. additionTo the residue was added 50 ml of ethyl ether

Sources & evidence

ORD record
ord-2ccafadcb2844dc08c45f76fc71cc954
Source dataset
uspto-grants-1985_12
Patent number
US04559361

Reaction notes

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