2,3-Dihydroxybutanedioic Acid → (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)(=O)C(C(C(O)=O)O)O.C(C(C(C([O-])=O)O)O)([O-])=O.[NH4+].[NH4+]>>[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
4
Procedure
first by converting it to a mixture of diastereoisomeric salts of N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate via reaction with optically active tartaric acid in the molar ratio 1:2 relative to the substance of formula III or with optically active alkali metal tartrate or ammonium tartrate, or an alkylammonium tartrate, of formula IV, in the molar ratio 1:1, followed by isolating the salt (S)—N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate (2:1) (Scheme 2) from the mixture of the diastereoisomeric salts in an organic solvent, water or a mixture thereof
Sources & evidence
- ORD record
- ord-918590d0f8b64912acd3db781fa829d6
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207356B2
Reaction notes
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