N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate → (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

HRID 222783Notes

Reaction equation

HRID 222783 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]>O1CCCC1.O>[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

Reactant 1

HCID 86625060N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

Product 1

HCID 86625059(S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(RS)—N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate (773 g, 1 mole) is dissolved in warm tetrahydrofuran (1500 ml) with addition of water (40 ml). After cooling down to ambient temperature, the mixture is stirred for 24 h. The precipitated crystals are recrystallized once more in tetrahydrofuran (400 ml) with an addition of water (12 ml) following the same procedure. Yield: 170 g (22%). Optical purity: 99.5% ee (CE).

Workup

  1. customThe precipitated crystals are recrystallized once more in tetrahydrofuran (400 ml) with an addition of water (12 ml)

Sources & evidence

ORD record
ord-2eef668e0cad4dd7b20d8a53e636fd70
Source dataset
uspto-grants-2012_06
Patent number
US08207356B2

Reaction notes

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