(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol → Quinidinone
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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).