Methanesulfonic Acid → HCID 19610770, compound

HRID 1602191Notes

Reaction equation

HRID 1602191 reaction equation
Cl.[N:2]12CCC([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[CH3:11][O:12][C:13]([O:16][CH3:17])([CH3:15])[CH3:14].CS(O)(=O)=O>P([O-])([O-])([O-])=O>[CH3:11][O:12][C:13]1([O:16][CH3:17])[CH:15]2[CH2:6][CH2:7][N:2]([CH2:3][CH2:4]2)[CH2:14]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 64952,2-DimethoxypropaneHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 19610770HCID 19610770, compound

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A mixture of 3-quinuclidinone hydrochloride (5.00 g, 30.9 mmol), 2,2 dimethoxypropane (50 ml), and methanesulfonic acid (0.1 ml) was refluxed for 8 h. The reaction mixture was poured in pH 7.4 phosphate buffer (20 ml) and washed 4 times with ethyl acetate. The aqueous phase was made basic by the addition of 4 M NaOH. Extraction with 3 portions of ethyl acetate gave, after drying and evaporation the title compound as a colorless oil. Yield 4.00 g (75%).

Workup

  1. temperaturewas refluxed for 8 h
  2. washwashed 4 times with ethyl acetate
  3. additionThe aqueous phase was made basic by the addition of 4 M NaOH
  4. extractionExtraction with 3 portions of ethyl acetate
  5. customgave
  6. customafter drying
  7. customevaporation the title compound as a colorless oil

Sources & evidence

ORD record
ord-fd3ff2d623e444c38c2f5556a8a2d0bd
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

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