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

HRID 2234232Notes

Reaction equation

HRID 2234232 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>[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

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 1

HCID 8028TetrahydrofuranSolvent

Procedure

(RS)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-D-tartrate (461 g) is dissolved in tetrahydrofuran (900 ml) while hot. After cooling down to lab temperature, the mixture is stirred for 24 hours. The precipitated crystals are re-crystallized from tetrahydrofuran (400 ml) once more using the same procedure. The yield is 117 g (25%). Optical purity is 99% ee (CE).

Workup

  1. temperatureAfter cooling down to lab temperature
  2. customThe precipitated crystals are re-crystallized from tetrahydrofuran (400 ml)

Sources & evidence

ORD record
ord-da3b1a9d355d424fb640704e86298b29
Source dataset
uspto-grants-2010_05
Patent number
US07709662B2

Reaction notes

Loading…