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

HRID 46807

Reaction equation

HRID 46807 reaction equation
C1(=O)C2C(C3C(C=2)=CC=CC=3)=CC=C1.[Na].[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]2[N:27]=[CH:26][CH:25]=[C:24]([C@H:28]([OH:39])[C@@H:29]3[N:34]4[CH2:35][C@H:36]([CH:37]=[CH2:38])[CH:31]([CH2:32][CH2:33]4)[CH2:30]3)[C:22]=2[CH:23]=1>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]2[N:27]=[CH:26][CH:25]=[C:24]([C:28]([C@@H:29]3[N:34]4[CH2:35][C@H:36]([CH:37]=[CH2:38])[C@@H:31]([CH2:32][CH2:33]4)[CH2:30]3)=[O:39])[C:22]=2[CH:23]=1

Participants

5

Reactant 3

HCID 5953(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanolHCID 5360545SodiumHCID 22281833Fluoreneone

Product 1

HCID 84497Quinidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of fluorenone ketyl was prepared by mixing 9 g. of fluorenone and 6.5 g. of sodium in anhydrous toluene. To this solution was added a hot solution of 37 g. of anhydrous quinidine base in 150 ml. of anhydrous toluene. After 15 minutes at reflux, the reaction was complete. After extraction and neutralization treatments as in Example I, 36 g. of pure quinidinone (TLC) was obtained (97% of theory).

Workup

  1. additionby mixing 9 g
  2. additionTo this solution was added a hot solution of 37 g
  3. temperatureAfter 15 minutes at reflux
  4. extractionAfter extraction and neutralization treatments as in Example I, 36 g

Sources & evidence

ORD record
ord-2e349f16a0ab4c7baaf37321e4e4dae6
Source dataset
uspto-grants-1979_11
Patent number
US04175192

Linked notes

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