4-benzyloxy-alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol → alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-4-hydroxybenzyl alcohol

HRID 1462358Notes

Reaction equation

HRID 1462358 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]([OH:29])[CH2:14][NH:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([C:26](=[O:28])[NH2:27])[CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:26]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[OH:25])[O:18][CH2:17][CH2:16][NH:15][CH2:14][CH:13]([OH:29])[C:12]1[CH:30]=[CH:31][C:9]([OH:8])=[CH:10][CH:11]=1)(=[O:28])[NH2:27]

Participants

4

Reactant 1

HCID 541676984-benzyloxy-alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol

Product 1

HCID 53708674alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-4-hydroxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7.2 g of 4-benzyloxy-α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol in 200 ml of methanol is hydrogenated analogously to Example 7 in the presence of palladium-on-charcoal catalyst (5%). Evaporation of the filtered solution yields crude α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-4-hydroxybenzyl alcohol, which after recrystallisation from methanol/isopropanol melts at 194°-196°.

Workup

  1. customEvaporation of the filtered solution

Sources & evidence

ORD record
ord-5297b765c53a4ab080575d4d9efdd9ab
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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