(+-)-3-Quinuclidinol → HCID 19770959, compound

HRID 1589846Notes

Reaction equation

HRID 1589846 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Na].[CH2:11]([C:13]1[N:18]2[N:19]=[CH:20][C:21]([C:22](OCC)=[O:23])=[C:17]2[CH:16]=[CH:15][CH:14]=1)[CH3:12]>C1C=CC=CC=1>[CH2:11]([C:13]1[N:18]2[N:19]=[CH:20][C:21]([C:22]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[O:23])=[C:17]2[CH:16]=[CH:15][CH:14]=1)[CH3:12]

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 19770953HCID 19770953, compound

Product 1

HCID 19770959HCID 19770959, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After suspension of 140 mg (1.10 mmol) of 3-quinuclidinol in 20 ml of benzene was refluxed for 0.5 hour by using a Dean-Stark apparatus, 0.05 g of metal sodium was added and the resultant mixture was refluxed under stirring for further 1.5 hours. Unreacted sodium was removed and 80 mg (0.37 mmol) of ethyl 7-ethylpyrazolo[1,5-a]pyridine-3-carboxylate were added, followed by heating under reflux for 12 hours. The solvent of the reaction mixture was distilled off under reduced pressure and the residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1), whereby 100 mg (0.33 mmol) of the title compound were obtained as an oily substance (yield: 91%).

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. additionwas added
  3. customwas removed
  4. temperatureby heating
  5. temperatureunder reflux for 12 hours
  6. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-46df1b07fb234e86a4132bd883cd5c25
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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