hydroxylamine-O-sulfonic acid → 1,4-Diazatricyclo[4.3.1.13,8]undecan-5-one
Reaction equation
[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C:4]3=[O:11])[CH2:2]1)[CH2:8]2.[NH2:12]OS(O)(=O)=O>C(O)=O>[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([NH:12][C:4]3=[O:11])[CH2:2]1)[CH2:8]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of azaadamantan-4-one (2.0 g, 13.2 mmol; Synthesis 1992, 1080) in formic acid (10 mL) at room temperature was treated with a solution of hydroxylamine-O-sulfonic acid (2.24 g, 19.8 mmol; Aldrich) in formic acid (7 mL) added dropwise. The resulting mixture was then heated at reflux for 3.5 hours. After cooling the reaction mixture to room temperature, the solvent was removed under reduced pressure, and the resulting oil was diluted with 1 NNaOH and extracted with chloroform (3×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography over silica gel (115 g), eluting with 5-10% methanol (containing 1% ammonium hydroxide)-chloroform to afford the title compound: MS (DCI/NH3) m/z 167 (M+H)+, 184 (M+NH4)+.