Sodium Bicarbonate → (+)-Sibutramine

HRID 2183830Notes

Reaction equation

HRID 2183830 reaction equation
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]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 937011(-)-SibutramineHCID 116679492,3-Bis(benzoyloxy)butanedioic acid--water (1/1)

Product 1

HCID 667542(+)-Sibutramine

Procedure

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.

Workup

  1. extractionextracted with chloroform

Sources & evidence

ORD record
ord-30fba883652741d893f2fe1c2bae2c44
Source dataset
uspto-grants-2005_05
Patent number
US06900245B2

Reaction notes

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