Perchloric Acid → HCID 14257763, compound

Participants

Reaction Steps

7-Benzyl-3-selena-7-azabicyclo[3.3.1]nonan-9-one (0.65 g, 2.2 mmol) was dissolved in dry benzene (250 mL). Perchloric acid (60%, 1.0 g, 6.0 mmol) was added dropwise very slowly with cooling and swirling. This precipitated an orange solid which adhered to the side of the flask. The benzene was decanted and the solid was recrystallized (95% ethanol) to give 7-benzyl-3-selena-7-azabicyclo[3.3.1]nonan-9,9-diol hydroperchlorate (0.62 g, 68.3%) as white needles: mp 214.0°-216.0° C. (dec); IR (KBr) cm-1 3430, 1080; 1H NMR (DMSO-d6) δ2.43 [br s, 2H, H(2,4)ax ], 2.72 [br d, 2H, H(2,4)eq ], 3.22-3.50 [m, 6H, H(6,8)ax, H(1,5), OH], 3.50-3.64 [m, 2H, H(6,8)eq ], 4.35 [d, 2H, H(10-NCH2)], 7.40-7.70 [m, 5H, ArH], 9.20 [br s, 1H, H(7)]; 13C NMR (DMSO-d6) ppm 21.1 [C(2,4)], 34.7 [C(1,5)], 54.9 [C(6,8)], 60.1 [C(10)-NCH2)], 92.5 [C(9)], 129.2, 129.7, 130.0, 130.5 [ArC]; 15N NMR (DMSO-d6) ppm 51.88 [N(7)]; 77Se NMR (DMSO-d6) ppm 62.39 [Se(3)]. Analysis calculated for C14H20NClSeO6 : N, 3.39; Se, 19.13. Found: N, 3.20; Se, 19.51. ##STR28##

Provenance & Evidence