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

HRID 46668

反応式

HRID 46668 の反応式
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

参加物

5

反応物 3

HCID 1049PyridineHCID 84497QuinidinoneHCID 21225700Diisobutylaluminumhydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-929afc279f8a4cc78c9504bf9daedd5e
出典データセット
uspto-grants-1979_11
特許番号
US04174449

関連ノート

読み込み中…