N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate → (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate
Reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24]>C(O)C>[CH3:1][N:2]([CH2:4][CH2:5][C@H:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(RS)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-D-tartrate (461 g) is dissolved in ethanol (700 ml) under reflux. After gradual cooling to lab temperature, the mixture is stirred for 164 hours. The precipitated crystals are sucked off and washed with ethanol. The yield is 150 g (32%). Optical purity is 98% ee (CE).
Workup
- temperature