3-Quinuclidinol, (+)- → HCID 9947760, compound
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
After a suspension of 760 mg (0.76 mmol) of (S)-(+)-3-quinuclidinol, which had been prepared in accordance with the procedure disclosed in "Eur. J. Med. Chem.", 14, 111-114 (1979), in 60 ml of benzene was refluxed for 1.5 hours by using a Dean-Stark apparatus, 0.2 g of metal sodium was added and the resultant mixture was refluxed under stirring for further 2.5 hours. Unreacted sodium was removed and 440 mg (2.2 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 500 mg (1.8 mmol) of the title compound were obtained as white crystals (yield: 81%).
Workup
- customhad been prepared in accordance with the procedure
- additionwas added
- customwas removed
- temperatureby heating
- temperatureunder reflux for 24 hours
- distillationThe solvent of the reaction mixture was distilled off under reduced pressure
- customthe residue was purified by chromatography on a silica gel column (chloroform:methanol=10:1)
Sources & evidence
- ORD record
- ord-7d226d29bace4ec1a91f665a296f3411
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05200415
Reaction notes
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