hydroxylamine-O-sulfonic acid → HCID 49870652, compound

HRID 80416Notes

Reaction equation

HRID 80416 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]2

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-one

Product 1

HCID 49870652HCID 49870652, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

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)+.

Workup

  1. additionadded dropwise
  2. temperatureThe resulting mixture was then heated
  3. temperatureat reflux for 3.5 hours
  4. customthe solvent was removed under reduced pressure
  5. additionthe resulting oil was diluted with 1 NNaOH
  6. extractionextracted with chloroform (3×)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude material was purified by flash chromatography over silica gel (115 g)
  12. washeluting with 5-10% methanol (containing 1% ammonium hydroxide)-chloroform

Sources & evidence

ORD record
ord-a5725a91c1784baf9c89d46ddf490049
Source dataset
uspto-grants-2014_09
Patent number
US08846661B2

Reaction notes

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