[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=O)[CH2:3]1)[CH2:9]2.Cl.[NH2:14][OH:15]>CCO.[OH-].[Na+]>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[N:14][OH:15])[CH2:3]1)[CH2:9]25-Hydroxy-2-admantanone (15 g, 90.2 mmol, CAS #: 20098-14-0, purchased from TCI) was dissolved in EtOH (100 mL) and added to a solution of hydroxylamine hydrochloride (10 g, 143.9 mmol) in 1N NaOH (80 mL). The mixture was heated at 100° C. for 2 hours. The EtOH was evaporated, and water and dichloromethane were added. The resulting mixture was stirred for 10 min and then filtered. The solid was collected. The resulting mixture was separated. The aqueous layer was further extracted twice with dichloromethane. The combined organic phases were concentrated under high vacuum. The resulting residue was combined with the solid from the filtration. Crystallization from EtOAc gave 5-hydroxy-adamantan-2-one oxime (12 g, 73%). Mass spectrum: m/z: 182 (M+1).
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