Water → HCID 21832191, compound

HRID 1901154Notes

Reaction equation

HRID 1901154 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:29])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([OH:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.O>C1C=CC=CC=1>[CH3:27][O:26][C:24]([CH:23]([OH:28])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:13]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:29])=[CH:17][CH:18]=1)=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 21832160HCID 21832160, compound

Product 1

HCID 21832191HCID 21832191, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 1.16 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 1.71 g of methyl 3-[4-(2-oxopropoxy)phenyl]lactate (prepared as described in Preparation 6) and 40 ml of benzene was heated under reflux for 3.5 hours, whilst the water being formed during the reaction was continuously removed. After completion of the reaction, the benzene used in the reaction was removed by distillation under reduced pressure, and the residue was dissolved in 50 ml of absolute methanol. 2.04 g of sodium cyanoborohydride were added, whilst ice-cooling, to the solution, and the resulting mixture was allowed to react overnight at room temperature. At the end of this time, methanol was removed by distillation under reduced pressure, and the resulting residue was mixed with ethyl acetate and with an aqueous solution of sodium chloride. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 1.9 g of the title compound having an Rf=0.30 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Workup

  1. temperaturewas heated
  2. customformed during the reaction
  3. customwas continuously removed
  4. customAfter completion of the reaction
  5. customwas removed by distillation under reduced pressure
  6. dissolutionthe residue was dissolved in 50 ml of absolute methanol
  7. addition2.04 g of sodium cyanoborohydride were added, whilst ice-
  8. temperaturecooling, to the solution
  9. customto react overnight at room temperature
  10. customAt the end of this time, methanol was removed by distillation under reduced pressure
  11. additionthe resulting residue was mixed with ethyl acetate and with an aqueous solution of sodium chloride
  12. customThe ethyl acetate layer was separated
  13. washwashed with an aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe solvent was then removed by distillation under reduced pressure
  16. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-cc624ed866ae43a38bb80c4bceba5868
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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