Galantamin → (+)-Narwedine

HRID 22461

반응식

HRID 22461 반응식
[CH3:1][N:2]1[CH2:21][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]3[C:14]=2[C@:5]2([C@@H:11]([O:12]3)[CH2:10][C:8](=[O:9])[CH:7]=[CH:6]2)[CH2:4][CH2:3]1.CN1CC2C=CC(OC)=C3C=2[C@]2([C@@H](O3)C[C@@H](O)C=C2)CC1.CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1.CN1CC2=C3C(=C(OC)C=C2)O[C@H]2[C@@]3(C=C[C@@H](O)C2)CC1>>[CH3:1][N:2]1[CH2:21][C:15]2=[C:14]3[C:13](=[C:18]([O:19][CH3:20])[CH:17]=[CH:16]2)[O:12][C@H:11]2[C@@:5]3([CH:6]=[CH:7][C:8]([CH2:10]2)=[O:9])[CH2:4][CH2:3]1

참가 물질

5

반응물 4

HCID 3449GalantaminHCID 9651(-)-GalantamineHCID 906210Galantamine, (+)-HCID 10356588Narwedine5회

생성물 1

HCID 441596(+)-Narwedine

실험 절차

Once dissolved, the racemic narwedine mixture is maintained at a temperature of 25° C. to 70° C., preferably 40° C. to 60° C., and the crystals of enantiomeric narwedine, enantiomeric galanthamine, or enantiomeric epigalanthamine in an amount of from 0.1% to 2%, preferably 0.2% to 1% by weight relative to the amount of narwedine to be resolved are added. If (-)-narwedine is to be produced, the crystals added here are either (-)-narwedine, (+)-galanthamine, or (+)-epigalanthamine. If the reaction is to produce (+)-narwedine, the crystal used here are (+)-narwedine, (-)-galanthamine or (-)-epigalanthamine. Since the end result of the next step (the reduction to (-)-galanthamine) is intended to be as free as possible of epigalanthamine and (+)-galanthamine, (-)-narwedine is the most preferred crystal to use to generate additional (-)-narwedine so long as it is available. The temperature is then dropped to 25° to 70° C., preferably 40° C. to 60° C. and held there for 5-24 hours, preferably 12-18 hours, most preferably about 16 hours.

후처리

  1. dissolutionOnce dissolved
  2. customto be produced
  3. additionthe crystals added here

출처 및 근거

ORD 기록
ord-f6205e02a6c94ac6bce8060a9027a0b6
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428159

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