N-[2-(4-Benzoyloxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine → N-[2-(4-Hydroxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

HRID 1388741Notes

Reaction equation

HRID 1388741 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][CH2:20][CH:21]([C:23]2[O:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[CH:27]=2)[OH:22])[CH3:18])=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH:17]([NH:19][CH2:20][CH:21]([C:23]2[O:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[CH:27]=2)[OH:22])[CH3:18])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 20470050N-[2-(4-Benzoyloxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 12816512N-[2-(4-Hydroxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(4-Benzoyloxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine (2 g) in ethyl acetate (150 ml) was hydrogenated over 5% palladium on charcoal at atmospheric pressure. After uptake of hydrogen had ceased the mixture was filtered and the filtrate evaporated to dryness. Chromatography of the residual oil on Kieselgel 60 (5% methanol in dichloromethane) gave the title compound, m.p. 135°-8°, (EtOAc-ether), as a 94:6 mixture of diastereoisomers.

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-ca4e6b2e91d245f797dad6261c1c3021
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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