Perchloric Acid → HCID 14257763, compound

HRID 326446Notes

Reaction equation

HRID 326446 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[C:16](=[O:17])[CH:10]([CH2:11][Se:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=[O:19]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:15][CH:14]2[C:16]([OH:19])([OH:17])[CH:10]([CH2:11][Se:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 14257719HCID 14257719, compound

Product 1

HCID 14257763HCID 14257763, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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##

Workup

  1. temperaturewith cooling
  2. customThis precipitated an orange solid which
  3. customThe benzene was decanted
  4. customthe solid was recrystallized (95% ethanol)

Sources & evidence

ORD record
ord-fd935ffeb58f4d24a5152c9ca780a6e8
Source dataset
uspto-grants-1993_12
Patent number
US05268481

Reaction notes

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