3-Quinuclidinol, (-)- → HCID 54088674, compound

HRID 1589839Notes

Reaction equation

HRID 1589839 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H: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][C@@H: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 914043-Quinuclidinol, (-)-HCID 5360545Sodium2×HCID 19770966Ethyl 7-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 54088674HCID 54088674, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After a suspension of 90 mg (0.71 mmol) of (R)-(-)-3-quinuclidinol, which had been prepared in accordance with the procedure disclosed in "Eur. J. Med. Chem.", 14, 111-114 (1979), in 15 ml of benzene was refluxed for 1.5 hours by using a Dean-Stark apparatus, 0.05 g of metal sodium was added and the resultant mixture was refluxed under stirring for further 2.5 hours. Unreacted sodium was removed and 100 mg (0.49 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 15 mg (0.05 mmol) of the title compound were obtained as white crystals (yield: 12%).

Workup

  1. customhad been prepared in accordance with the procedure
  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-8e6ffd763ea74427baf7a9797d60c7c1
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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