Pyridine → (S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

HRID 46668

Reaction equation

HRID 46668 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]=[CH:17][CH:16]=[C:15]([C:19]([C@@H:21]3[N:26]4[CH2:27][C@H:28]([CH:29]=[CH2:30])[C@@H:23]([CH2:24][CH2:25]4)[CH2:22]3)=[O:20])[C:13]=2[CH:14]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]=[CH:17][CH:16]=[C:15]([C@H:19]([OH:20])[C@@H:21]3[N:26]4[CH2:27][C@H:28]([CH:29]=[CH2:30])[CH:23]([CH2:24][CH2:25]4)[CH2:22]3)[C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 84497QuinidinoneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 5953(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

600 ml. anhydrous pyridine, 100 g. crystallized quinidinone, and 300 ml. 25% solution of diisobutylaluminum hydride (DIBAH) in toluene were in a reaction vessel and the reaction was allowed to proceed until the reduction was completed as indicated by thin layer chromatography. The mixture was then heated under vacuum (25 mm Hg) to remove the pyridine. The reaction mixture was then treated with 750 ml. of a 50/50 mixture of water and ethanol, and after refluxing for 2 hours and cooling, 92.7 g. of quinidine base were obtained, exhibiting a melting point of 174.5° C.

Workup

  1. temperatureThe mixture was then heated under vacuum (25 mm Hg)
  2. customto remove the pyridine
  3. additionThe reaction mixture was then treated with 750 ml
  4. additionof a 50/50 mixture of water and ethanol
  5. temperatureafter refluxing for 2 hours
  6. temperaturecooling

Sources & evidence

ORD record
ord-929afc279f8a4cc78c9504bf9daedd5e
Source dataset
uspto-grants-1979_11
Patent number
US04174449

Linked notes

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