Ammonia → 4-Aminoadamantan-1-ol

To a solution of 5-hydroxy-2-adamantanone (10.2 g) in 8M ammonia (in methanol, 50 ml), 10% palladium on activated carbon (1.00 g) was added and stirred under a hydrogen atmosphere at room temperature for 15 hours. After the reaction mixture was filtered, the solvent was distilled off under reduced pressure and the resulting residue was purified by NH silica gel column chromatography (eluting solvent: chloroform alone→chloroform:methanol=9:1) to give 4-aminoadamantan-1-ol (10.2 g, E-form:Z-form=4:1). 4-Aminoadamantan-1-ol thus obtained (10.2 g) was dissolved by heating in tetrahydrofuran (50 ml), and 4M hydrochloric acid (in 1,4-dioxane, 20 ml) was added thereto, followed by stirring at room temperature for 16 hours. The precipitated solid was collected by filtration to give 4-aminoadamantan-1-ol hydrochloride (12.1 g, E-form:Z-form=4:1). The resulting E/Z mixture (9.15 g) was dissolved by heating in ethanol (450 ml) and water (35.5 ml), and stirred at room temperature for 2 days. The precipitated solid was collected by filtration to give the titled compound, i.e., E-4-aminoadamantan-1-ol hydrochloride (3.59 g) as a colorless powder.

1. filtrationAfter the reaction mixture was filtered
2. distillationthe solvent was distilled off under reduced pressure
3. customthe resulting residue was purified by NH silica gel column chromatography (
4. washeluting solvent

ORD record

ord-6912dc4362334dbf9e15bd3efda9a6cd

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222417B2