(+-)-3-Quinuclidinol → HCID 19038078, compound

HRID 263456Notes

Reaction equation

HRID 263456 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[H-].[Na+].Cl[C:13]1[C:17]([Cl:18])=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:15][N:14]=1>CN(C)C=O>[Cl:18][C:17]1[C:13]([O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[N:14][O:15][C:16]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 190380973,4-Dichloro-5-phenylisoxazole

Product 1

HCID 19038078HCID 19038078, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.96 g of 3-quinuclidinol in 30 ml of dimethylformamide was cooled to 5° C. in an atmosphere of nitrogen. 0.67 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was then added to the cooled solution, and then the solution was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was cooled to 5° C., and 3.0 g of 3,4-dichloro-5-phenylisoxazole were added. The resulting mixture was then stirred at room temperature for 5 hours. At the end of this time, it was poured into 100 ml of ice-water and extracted twice, each time with 100 ml of ethyl acetate. The ethyl acetate extracts were combined and washed twice, each time with 100 ml of a 10% w/v aqueous solution of sodium chloride; they were then dried over anhydrous magnesium sulfate, after which the drying agent was removed by filtration. The solvent was then removed from the filtrate by distillation under reduced pressure. The residue thus obtained was purified by column chromatography through silica gel using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to afford 4.21 g (yield 98.7%) of the title compound as a colorless and transparent oil.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled to 5° C.
  2. stirringThe resulting mixture was then stirred at room temperature for 5 hours
  3. extractionextracted twice
  4. washwashed twice
  5. dry with materialthey were then dried over anhydrous magnesium sulfate
  6. customafter which the drying agent was removed by filtration
  7. customThe solvent was then removed from the filtrate by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography through silica gel using a 10:1
  10. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-90be807dfaf44372bb5ed69d601b3729
Source dataset
uspto-grants-1997_07
Patent number
US05643923

Reaction notes

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