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 1388736노트

반응식

HRID 1388736 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fade235ea703479a991575f0340753c3
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04432993

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