Sibutramine → (-)-Sibutramine
Reaction equation
[CH3:1][CH:2]([CH2:4][CH:5]([N:17]([CH3:19])[CH3:18])[C:6]1([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:3]>C(OCC)(=O)C>[CH3:3][CH:2]([CH2:4][C@H:5]([N:17]([CH3:18])[CH3:19])[C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH2:9]1)[CH3:1]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
12.3 g of racemic sibutramine was dissolved in 85 ml of ethyl acetate, L-DBTA dissolved in 85 ml of ethyl acetate was added thereto. The reaction mixture was heated under reflux, cooled to room temperature and then filtered to obtain crystals (ee: about 85%). And then, the crystals were suspended in 220 ml of ethyl acetate, and heated under reflux to obtain solids. The solids were recrystallized from 450 ml of isopropyl alcohol to obtain L-DBTA salt of (−)-sibutramine (ee: ≧99.3%). The L-DBTA salt of (−)-sibutramine was neutralized with saturated sodium bicarbonate, and then extracted with chloroform to obtain (−)-sibutramine free base.
Workup
- additionwas added