(+-)-3-Quinuclidinol → HCID 19770967, compound

HRID 1589837Notes

Reaction equation

HRID 1589837 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[N:17]2[N:18]=[CH:19][C:20]([C:21](OCC)=[O:22])=[C:16]2[CH:15]=[CH:14][CH:13]=1>C1C=CC=CC=1>[CH3:11][C:12]1[N:17]2[N:18]=[CH:19][C:20]([C:21]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[O:22])=[C:16]2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 19770966Ethyl 7-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 19770967HCID 19770967, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After a suspension of 370 mg (2.9 mmol) of 3-quinuclidinol (product of Aldrich Chemical Co., Inc.) in 30 ml of benzene was refluxed for 1.5 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 2.5 hours. Unreacted sodium was removed and 200 mg (0.98 mmol) of ethyl 7-methylpyrazolo[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 240 mg (0.84 mmol) of the title compound were obtained as white crystals (yield: 86%).

Workup

  1. temperaturewas refluxed for 1.5 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-bc9bd81d48c240d2af7bdb6d49a88419
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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