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

HRID 46668

반응식

HRID 46668 반응식
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

참가 물질

5

반응물 3

HCID 1049PyridineHCID 84497QuinidinoneHCID 21225700Diisobutylaluminumhydride

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-929afc279f8a4cc78c9504bf9daedd5e
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04174449

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