Water → HCID 19874519, compound

HRID 465434Notes

Reaction equation

HRID 465434 reaction equation
[CH2:1]([C:5]1[CH:21]=[CH:20][C:8]([O:9][CH2:10][C:11]2[O:15][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.[OH:22][CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[CH2:24][NH2:25].O>C1C=CC=CC=1>[Cl:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH:23]([OH:22])[CH2:24][NH:25][CH:2]([CH3:4])[CH2:1][C:5]1[CH:21]=[CH:20][C:8]([O:9][CH2:10][C:11]2[O:15][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 19874534HCID 19874534, compound

Product 1

HCID 19874519HCID 19874519, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 5-[4-acetonylphenoxymethyl]furan-2-carboxylate (1.76 g) and 2-hydroxy-2-(3-chlorophenyl) ethanamine (1.05 g) in dry benzene (100 ml) was heated under reflux with azeotropic removal of water, for 2 hr. The solvent was evaporated and sodium borohydride (2 g) added, in portions, to a stirred solution of the residual oil in methanol (80 ml) with cooling in ice. The mixture was stirred at ambient temperature for 3 hr. the solvent was evaporated and the residue was partitioned between water and dichloromethane. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with methanol:chloroform (4:96) gave an oil which was crystallised from n-hexane to give methyl 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]furan-2-carboxylate, m.pt 75°-86° C., as a 19:81 mixture of diastereoisomers. The mother liquor was evaporated; crystallisation from Petroleum ether (60:80)--ether gave a second crop, m.pt. 75°-83° C., as a 55:45 mixture of diastereoisomers.

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. additionsodium borohydride (2 g) added, in portions, to a stirred solution of the residual oil in methanol (80 ml)
  4. temperaturewith cooling in ice
  5. customthe solvent was evaporated
  6. customthe residue was partitioned between water and dichloromethane
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated to an oil which
  9. customwas purified by column chromatography on silica gel
  10. washElution with methanol:chloroform (4:96)
  11. customgave an oil which
  12. customwas crystallised from n-hexane

Sources & evidence

ORD record
ord-4b7b902b8a8c497eb5769956eaf1edb1
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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