(-)-Galantamine → 4'-O,N-dimethylnorbelladine

HRID 1699434Notes

Reaction equation

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

Participants

Reactant 2

HCID 9651(-)-Galantamine

HCID 10356588Narwedine

Product 1

HCID 2802834'-O,N-dimethylnorbelladine

Procedure

Barton and Kirby, J. Chem. Soc. (1962) 806, disclose the first synthetic route to (−)−galanthamine from racemic narwedine which had been prepared in very low yield from N-(3-hydroxy-4-methoxy-benzyl)-N-methyl-2-(4-hydroxyphenyl)-ethylamine. They found that (−)−narwedine crystallised preferentially when (+)−galanthamine or a mixture of (+)−galanthamine and (+)−epigalanthamine was present, and used this to resolve racemic narwedine.

Workup

customhad been prepared

Sources & evidence

ORD record: ord-81c0dc0c9d0b4af1a455b080d0a3b065
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346618B1

Reaction notes

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