(+-)-3-Quinuclidinol → HCID 19770977, compound

HRID 1589841Notes

Reaction equation

HRID 1589841 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Na].[CH3:11][C:12]1[C:21]([C:22](OCC)=[O:23])=[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[N:14]2[N:13]=1>C1C=CC=CC=1>[CH3:11][C:12]1[C:21]([C:22]([O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[O:23])=[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[N:14]2[N:13]=1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 21827510HCID 21827510, compound

Product 1

HCID 19770977HCID 19770977, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After a suspension of 350 mg (2.76 mmol) of 3-quinuclidinol in 30 ml of benzene was refluxed for 1.0 hours by using a Dean-Stark apparatus, 0.1 g of metal sodium was added and the resultant mixture was refluxed under stirring for further 3 hours. Unreacted sodium was removed and 200 mg (0.92 mmol) of ethyl 2,7-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate were added, followed by heating under reflux for 24 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 60 mg (0.20 mmol) of the title compound were obtained as white crystals (yield: 22%).

Workup

  1. temperaturewas refluxed for 1.0 hours
  2. additionwas added
  3. customwas removed
  4. temperatureby heating
  5. temperatureunder reflux for 24 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-95992b1089374b248fa235e1f41bd3e5
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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