2-Amino-1-(1-benzofuran-2-yl)ethan-1-ol → N-[2-(4-[(E)-2-carbomethoxyethenyl]phenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

HRID 1388736Notes

Reaction equation

HRID 1388736 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:13])[CH2:11][NH2:12].[C:14](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=O)[CH3:28])=[CH:22][CH:21]=1)([O:16][CH3:17])=[O:15]>O>[C:14](/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH:27]([NH:12][CH2:11][CH:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[OH:13])[CH3:28])=[CH:24][CH:25]=1)([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-olHCID 198745324-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one

Product 1

HCID 12816503N-[2-(4-[(E)-2-carbomethoxyethenyl]phenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-benzofuranyl)-2-hydroxyethanamine (1.0 g) and 4-[(E)-2-carbomethoxyethenyl]phenyl propan-2-one (1.13 g) was heated under reflux using a Dean and Stark head until the theoretical amount of water had been removed. The solvent was evaporated, the residue dissolved in methanol (50 ml) and sodium borohydride (0.5 g) added. The solvent was evaporated, the residue partitioned between water and ethyl acetate and the organic layer dried (magnesium sulphate). Removal of the solvent gave an oil which was chromatographed on Kieselgel 60. Elution with 2% methanol-chloroform gave N-[2-(4-[(E)-2-carbomethoxyethenyl]phenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine, as a 54:46 mixture of diastereoisomers, m.p. 85-89 (cyclohexane).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customhad been removed
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in methanol (50 ml)
  6. additionsodium borohydride (0.5 g) added
  7. customThe solvent was evaporated
  8. customthe residue partitioned between water and ethyl acetate
  9. dry with materialthe organic layer dried (magnesium sulphate)
  10. customRemoval of the solvent
  11. customgave an oil which
  12. customwas chromatographed on Kieselgel 60
  13. washElution with 2% methanol-chloroform

Sources & evidence

ORD record
ord-fade235ea703479a991575f0340753c3
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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