Sibutramine → (-)-Sibutramine

HRID 2183829Notes

Reaction equation

HRID 2183829 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

HCID 5210Sibutramine

Product 1

HCID 937011(-)-Sibutramine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

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

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux
  4. filtrationfiltered
  5. customto obtain crystals (ee: about 85%)
  6. temperatureheated
  7. temperatureunder reflux
  8. customto obtain solids
  9. customThe solids were recrystallized from 450 ml of isopropyl alcohol

Sources & evidence

ORD record
ord-41e3c7a37d08478284aa5be43ed05d98
Source dataset
uspto-grants-2005_05
Patent number
US06900245B2

Reaction notes

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