Perchloric Acid → HCID 14257763, compound

HRID 1111517Notes

Reaction equation

HRID 1111517 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. ##STR29##

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-e0b7b97d7c474d7797d1473166dfffdf
Source dataset
uspto-grants-1990_12
Patent number
US04980468

Reaction notes

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