5-Hydroxy-adamantan-2-one oxime → 4-Aminoadamantan-1-ol

Participants

Reaction Steps

Rh/Al2O3 (2.3 g, 5 wt. %, 1.1 mmol) was added to a mixture of 5-hydroxy-admantane-2-one oxime (10 g, 55 mmol) in EtOH (100 mL) in a Parr hydrogenation bottle. The hydrogenation reaction was performed in a Parr hydrogenation instrument at 55 psi pressure of hydrogen at 50° C. for 48 hours. The disappearance of starting material and generation of the product were detected by LC-MS. The mixture was filtered through celite and concentrated under vacuum to dryness to give 4-amino-adamantan-1-ol (about 9 g, ˜98%) which was used for the next step without further purification. Mass spectrum: m/z: 168.1 (M+1).

Provenance & Evidence