(+-)-3-Quinuclidinol → HCID 68154748, compound

HRID 1020018Notes

Reaction equation

HRID 1020018 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[C:5]([C:14](Cl)=[O:15])[CH:4]=[CH:3]1.[OH:17][CH:18]1[CH:23]2[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]2)[CH2:19]1>N1C=CC=CC=1>[N:20]12[CH2:25][CH2:24][CH:23]([CH2:22][CH2:21]1)[CH:18]([O:17][C:14]([C:5]1[CH:4]=[CH:3][C:2](=[O:1])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=1)=[O:15])[CH2:19]2

Participants

4

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 86701177HCID 86701177, compound

Product 1

HCID 68154748HCID 68154748, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After dissolution of the mixed solution of 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carbonyl chloride obtained in Example 115-1 in 5 mL of pyridine, 231 mg (1.82 mmol) of 3-hydroxyquinuclidine was added thereto. Afterward, the resulting reaction solution was stirred at room temperature for about 3 days. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo. Without an additional purification process, the resulting compound was extracted three times with water and chloroform, and the organic phase was purified using liquid chromatography (chloroform:methanol: ammonia water=10:1:0.1) to obtain a target compound (Actual yield: 65 mg, Percent yield: 20%).

Workup

  1. additionwas added
  2. customAfterward, the resulting reaction solution
  3. customthe solvent was removed in vacuo
  4. extractionWithout an additional purification process, the resulting compound was extracted three times with water and chloroform
  5. customthe organic phase was purified
  6. customto obtain a target compound (Actual yield: 65 mg, Percent yield: 20%)

Sources & evidence

ORD record
ord-06cc0a50e3564aa49e4556e20468bf45
Source dataset
uspto-grants-2014_05
Patent number
US08716309B2

Reaction notes

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