HCID 19874578, compound → HCID 19874518, compound

HRID 465430Notes

Reaction equation

HRID 465430 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:17][NH:18][CH:19]([CH3:35])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[NH:31][CH2:32][CH2:33][N:34]=3)=[CH:24][CH:23]=2)[OH:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OC(=O)C)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:17][NH:18][CH:19]([CH3:35])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[NH:34][CH2:33][CH2:32][N:31]=3)=[CH:24][CH:23]=2)[OH:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 19874578HCID 19874578, compound

Product 1

HCID 19874518HCID 19874518, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-benzyloxy-α-[[[2-[4-((4,5-dihydro-1H-2-imidazolyl)methyloxy)phenoxy]-1-methylethyl]amino]methyl]benzenemethanol (1.5 g) in ethylacetate (80 ml) was hydrogenated at atmospheric pressure in the presence of 10% palladium on carbon. The reaction mixture was filtered and evaporated to a foam which was purified by column chromatography on alumina. Elution with methanol-chloroform (8:92) gave 4-hydroxy-α [[[2-[4-((4,5-dihydro-1H-2-imidazolyl)-methyloxy)phenoxy]-1-methylethyl]amino]methyl]benzene-methanol m.pt. 160°-180° C. (ethyl acetate), as a 40:60 mixture of diastereoisomers.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to a foam which
  3. customwas purified by column chromatography on alumina
  4. washElution with methanol-chloroform (8:92)

Sources & evidence

ORD record
ord-6ae7a744c96140ea9cf5568cff0b0bab
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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