(+-)-3-Quinuclidinol → HCID 19770962, compound

HRID 1589847Notes

Reaction equation

HRID 1589847 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:14]1[N:19]2[N:20]=[CH:21][C:22]([C:23](OCC)=[O:24])=[C:18]2[CH:17]=[CH:16][CH:15]=1)[CH2:12][CH3:13]>C1C=CC=CC=1>[CH2:11]([C:14]1[N:19]2[N:20]=[CH:21][C:22]([C:23]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[O:24])=[C:18]2[CH:17]=[CH:16][CH:15]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 19770956HCID 19770956, compound

Product 1

HCID 19770962HCID 19770962, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After a suspension of 330 mg (2.60 mmol) of 3-quinuclidinol in 30 ml of benzene was refluxed for 0.5 hour 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 hours. Unreacted sodium was removed and 200 mg (0.86 mmol) of ethyl 7-propylpyrazolo[1,5-a]pyridine-3-carboxylate were added, followed by heating under reflux for 20 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 230 mg (0.73 mmol) of the title compound were obtained as an oily substance (yield: 85%).

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. additionwas added
  3. customwas removed
  4. temperatureby heating
  5. temperatureunder reflux for 20 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-29f8542f33a9400aaa94096a98c6990b
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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