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

HRID 2050888Notes

Reaction equation

HRID 2050888 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.[O:18]([NH2:20])[CH3:19]>C(Cl)(Cl)Cl.O.CO>[CH3:19][O:18][N:20]=[CH:8][CH:9]1[CH:14]2[CH2:13][CH2:12][N:11]([CH2:16][CH2:15]2)[CH2:10]1

Participants

7

Reactant 3

HCID 24247Perchloric AcidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 537726003-Methoxy methylidene quinuclidine

Product 1

HCID 542801241-azabicyclo-[2,2,2]-octan-3-carboxaldehyde O-methyloxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

11 cm3 of a 70% aqueous solution of perchloric acid is added at ambient temperature to 4.6 g of 3-methoxy methylidene quinuclidine (Heterocycles 244, 4-971 (1986)) in solution in 46 cm3 of chloroform. After one hour of contact, 2.5 g of methoxylamine hydrochloride in 10 cm3 of water and 10 cm3 of methanol is added and the reaction medium is maintained in this way for one night, and is then concentrated, alkalized with 2N sodium hydroxide, extracted with ethyl acetate; the solvents are evaporated, and the residue is taken up in ethyl ether and filtered. The filtrate is distilled at 150° C. under 0.08 mbar and 3.2 g of expected product is obtained.

Workup

  1. temperaturethe reaction medium is maintained in this way for one night
  2. concentrationis then concentrated
  3. extractionextracted with ethyl acetate
  4. customthe solvents are evaporated
  5. filtrationfiltered
  6. distillationThe filtrate is distilled at 150° C. under 0.08 mbar

Sources & evidence

ORD record
ord-bcb23ef401674cc4bf769996f1e242d6
Source dataset
uspto-grants-1991_05
Patent number
US05015655

Reaction notes

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