Galanthamine N-Oxide → (-)-Galantamine

HRID 619015

反応式

HRID 619015 の反応式
[CH3:1][N+:2]1([O-])[CH2:18][C:16]2=[C:17]3[C:12](=[C:13]([O:19][CH3:20])[CH:14]=[CH:15]2)[O:11][C@@H:10]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:21])[CH2:9]2)[CH2:4][CH2:3]1>CO>[CH3:1][N:2]1[CH2:18][C:16]2[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]3[C:17]=2[C@:5]2([C@@H:10]([O:11]3)[CH2:9][C@@H:8]([OH:21])[CH:7]=[CH:6]2)[CH2:4][CH2:3]1

参加物

3

反応物 1

HCID 11748698Galanthamine N-Oxide

生成物 1

HCID 9651(-)-Galantamine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 1.73 g (5.7 mmoles) of galanthamine N-oxide and 3.17 g (11,4 mmoles, 2 eq) of FeSO4 --7H2O in 100ml of methanol is agitated under argon for 1.5 hours at 10° C. After the evaporation of the solvent, the residue is taken up again in dichloromethane, treated with a saturated aqueous solution of sodium hydrogencarbonate and extracted three times with dichloromethane. The organic phases are collected and washed with a saturated aqueous solution of sodium chloride, dried on sodium sulfate and evaporated. The crude product of the reaction is purified by flash chromatography on silica gel using the mixture of dichloromethane/methanol (80:20) as eluant. The least polar fraction yields galanthamine and the most polar fraction yields for the most part norgalanthamine in the form of a white foam (yield=76%).

後処理

  1. customAfter the evaporation of the solvent
  2. additiontreated with a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionextracted three times with dichloromethane
  4. customThe organic phases are collected
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. customdried on sodium sulfate
  7. customevaporated
  8. customThe crude product of the reaction is purified by flash chromatography on silica gel using
  9. additionthe mixture of dichloromethane/methanol (80:20) as eluant

出典と根拠

ORDレコード
ord-0c1322a7f47645ad923f4c026698e788
出典データセット
uspto-grants-1999_09
特許番号
US05958903

関連ノート

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