Narwedine → (+)-Narwedine

HRID 1699435Notes

Reaction equation

[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([C:7]([C@@:9]([C:25]([OH:27])=[O:26])([OH:24])[C@@:10]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:16])([OH:14])[C:11]([OH:13])=[O:12])=[O:8])=[CH:3][CH:2]=1.[CH3:29][N:30]1[CH2:49][C:43]2[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:41]3[C:42]=2[C@:33]2([C@@H:39]([O:40]3)[CH2:38][C:36](=[O:37])[CH:35]=[CH:34]2)[CH2:32][CH2:31]1>C(O)C>[CH3:29][N:30]1[CH2:49][C:43]2=[C:42]3[C:41](=[C:46]([O:47][CH3:48])[CH:45]=[CH:44]2)[O:40][C@H:39]2[C@@:33]3([CH:34]=[CH:35][C:36]([CH2:38]2)=[O:37])[CH2:32][CH2:31]1.[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([C:7]([C@@:9]([C:25]([O-:27])=[O:26])([OH:24])[C@@:10]([C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[O:16])([OH:14])[C:11]([O-:13])=[O:12])=[O:8])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Di-p-toluoyl-L-tartaric acid (1.35 g, 3.50 mmol) was dissolved in ethanol (10 ml) on heating to 40° C. and then synthetic racemic narwedine (1.00 g, 3.50 mmol) was added and the mixture was heated at reflux for 1 h then cooled to 40° C. and stirred for 16 hours at this temperature. The mixture was cooled to ambient temperature, stirred for 2 h and then the white solid was isolated by filtration to give the 1:1 diastereomeric salt [(+)−narwedine] [di-p-toluoyl-L-tartrate] (2.16 g, 92% yield, 96% e.e.).

Workup

temperaturethe mixture was heated
temperatureat reflux for 1 h
temperaturethen cooled to 40° C.
temperatureThe mixture was cooled to ambient temperature
stirringstirred for 2 h
customthe white solid was isolated by filtration

Sources & evidence

ORD record: ord-bab2e55dec3849c9bf10f9a01a981ab2
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346618B1

Reaction notes

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