Water → HCID 178437195, compound

Participants

Reaction Conditions

Reaction Steps

7.7 g (30 mmol) methyl 2-amino-3-(1H-imidazol-4-yl)butyrate hydrochloride are added at 0° C. to a stirred suspension of 3.4 g (90 mmol) lithium aluminium hydride in 125 ml tetrahydrofurane. Subsequently, the mixture is refluxed for 3 hours, cooled to 0° C. and and hydrolysed by addition of 6.5 ml water in 15 ml tetrahydrofurane. Stirring with 20 ml 5N sodium hydroxide solution affords a coarse-grained precipitate which is filtered off and extracted by means of 100 ml ethanol in 3 portions. Concentration of the fractions affords an oil which is treated with anhydrous ethanol to separate inorganic material. Filtration and evaporation yield 4 g (85.9%) 2-amino-3-(1H-imidazol-4-yl)butanol wich is converted into the oily dihydrochloride. An analytical sample is converted into dipicrate and recrystallized from ethanol/water. Yellow crystals, melting point 168° C.

Provenance & Evidence