Water → HCID 178437195, compound

HRID 1087289Notes

Reaction equation

Cl.[NH2:2][CH:3]([CH:8]([C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)[CH3:9])[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(O)C>[NH2:2][CH:3]([CH:8]([C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)[CH3:9])[CH2:4][OH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperatureSubsequently, the mixture is refluxed for 3 hours
customaffords a coarse-grained precipitate which
filtrationis filtered off
extractionextracted by means of 100 ml ethanol in 3 portions
customConcentration of the fractions affords an oil which
customto separate inorganic material
filtrationFiltration and evaporation yield 4 g (85.9%) 2-amino-3-(1H-imidazol-4-yl)butanol wich
customrecrystallized from ethanol/water

Sources & evidence

ORD record: ord-bcdc1922a08249beb66ee802a9159a0c
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034539

Reaction notes

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