Perchloric Acid → 1-azabicyclo-[2,2,2]-octan-3-carboxaldehyde O-ethyloxime

HRID 2050889Notes

Reaction equation

HRID 2050889 reaction equation
Cl(O)(=O)(=O)=O.CO[CH:8]=[C:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1.Cl.[CH2:18]([O:20][NH2:21])[CH3:19]>C(Cl)(Cl)Cl.CO.O>[CH2:18]([O:20][N:21]=[CH:8][CH:9]1[CH:14]2[CH2:13][CH2:12][N:11]([CH2:16][CH2:15]2)[CH2:10]1)[CH3:19]

Participants

7

Reactant 3

HCID 24247Perchloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 537726003-Methoxy methylidene quinuclidine

Product 1

HCID 538005971-azabicyclo-[2,2,2]-octan-3-carboxaldehyde O-ethyloxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4.8 cm3 of a 70% aqueous solution of perchloric acid is added at ambient temperature to 2 g of 3-methoxy methylidene quinuclidine in solution in 20 cm3 of chloroform. After agitating for one hour, 1.4 g of O-ethylhydroxylamine hydrochloride in 2.5 cm3 of methanol and 2.5 cm3 of water are added, and the reaction medium is maintained in this way for one night. After concentrating, alkalizing with sodium hydroxide, extracting with ethyl acetate, and distilling at 135° C. under 0.05 mbar, 2.05 g of expected product is obtained.

Workup

  1. temperaturethe reaction medium is maintained in this way for one night
  2. concentrationAfter concentrating
  3. extractionextracting with ethyl acetate
  4. distillationdistilling at 135° C. under 0.05 mbar

Sources & evidence

ORD record
ord-97a38e115fbb4006bfa2104bfba3e97b
Source dataset
uspto-grants-1991_05
Patent number
US05015655

Reaction notes

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