Sodium Bicarbonate → (+)-Sibutramine

Reaktionsgleichung

C1C=CC(C(O[C@H](C(O)=O)[C@H](OC(C2C=CC=CC=2)=O)C(O)=O)=O)=CC=1.O.[CH3:28][CH:29]([CH2:31][C@H:32]([N:44]([CH3:46])[CH3:45])[C:33]1([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[CH2:36][CH2:35][CH2:34]1)[CH3:30].C(=O)(O)[O-].[Na+]>>[CH3:30][CH:29]([CH2:31][C@@H:32]([N:44]([CH3:45])[CH3:46])[C:33]1([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[CH2:34][CH2:35][CH2:36]1)[CH3:28]

Komponenten

Edukt 3

HCID 516892Sodium Bicarbonate

HCID 937011(-)-Sibutramine

HCID 11667949(+)-Dibenzoyl-D-tartaric acid monohydrate

Produkt 1

HCID 667542(+)-Sibutramine

Versuchsvorschrift

The filtrate obtained by filtration after reacting with L-DBTA was neutralized to pH 8.5 with sodium hydroxide, and then extracted with chloroform to obtain (+)-sibutramine, which was nearly pure (+)-isomer. D-DBTA was added thereto to obtain crystals and the crystals were recrystallized from 450 ml of isopropyl alcohol to obtain D-DBTA salt of (+)-sibutramine (ee: ≧99.3%). The D-DBTA salt of (−)-sibutramine was neutralized to pH 8.5 with saturated sodium bicarbonate, and then extracted with chloroform to obtain (+)-sibutramine free base.