Water → HCID 21398996, compound

HRID 1439261Notes

Reaction equation

HRID 1439261 reaction equation
C([O:3][C:4](=O)[C@H:5]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:7]([NH:6][CH:5]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:4][OH:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22800156HCID 22800156, compound

Product 1

HCID 21398996HCID 21398996, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

55.5 gm (0.16 mol) of N-benzoyl-3-(3'-methoxy-4'-methyl-phenyl)-alanine ethyl ester (m.p. 133° C) were dissolved in 550 ml of absolute tetrahydrofuran, and the resulting solution was slowly added dropwise to a stirred suspension of 37 gm (0.98 mol) of lithium aluminum hydride in 1850 ml of tetrahydrofuran at room temperature in an atmosphere of nitrogen. The resulting mixture was refluxed for five hours, then allowed to stand overnight, and subsequently slowly admixed with water. The inorganic precipitate formed thereby was collected by vacuum filtration, washed with tetrahydrofuran, and the wash solution was combined with the filtrate. The tetrahydrofuran was distilled in vacuo out of the combined solution, the residue was taken up in ether, and the ethereal mixture was extracted with water. The ether phase was dried over sodium sulfate, the ether was distilled off, and the residue was recrystallized from petroleum ether, yielding 45.0 gm (97.5% of theory) of the free base 2-benzylamino-3-(3'-methoxy-4'-methyl-phenyl)-1-propanol.

Workup

  1. temperatureThe resulting mixture was refluxed for five hours
  2. customThe inorganic precipitate formed
  3. filtrationthereby was collected by vacuum filtration
  4. washwashed with tetrahydrofuran
  5. distillationThe tetrahydrofuran was distilled in vacuo out of the combined solution
  6. extractionthe ethereal mixture was extracted with water
  7. dry with materialThe ether phase was dried over sodium sulfate
  8. distillationthe ether was distilled off
  9. customthe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-9f366fb052b742a3924b0810cc1c5c92
Source dataset
uspto-grants-1977_11
Patent number
US04058642

Reaction notes

Loading…