Water → HCID 21398996, compound

Participants

Reaction Steps

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.

Provenance & Evidence