Sodium Hydroxide → 4-Azatricyclo[4.3.1.13,8]undecan-5-one

Participants

Reaction Steps

To a solution of 2-adamantanone (2.00 g) in formic acid (10 ml) was added dropwise a suspension of hydroxyamine-O-sulfonic acid (2.26 g) in formic acid (7 ml) under stirring at ambient temperature. The mixture was heated at reflux temperature for 3.5 hours. The reaction mixture was allowed to cool to room temperature, alkalined with 1N sodium hydroxide aqueous solution and extracted with chloroform twice. The combined extracts were washed with water and dried over sodium sulfate. Removal of the solvent gave 2-azatricyclo[4.3.1.14,8 ]undecan-3-one (2.14 g), which was used in a following reaction step without further purification.

Provenance & Evidence