Sodium Hydroxide → (-)-(S,S)-trans-Tramadol

HRID 2394Notes

Reaction equation

HRID 2394 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[CH3:11][N:12]([CH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@:16]1([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[OH:21])[CH3:13].[OH-].[Na+]>O>[CH3:13][N:12]([CH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@:16]1([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[OH:21])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15388950(1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate

Product 1

HCID 667511(-)-(S,S)-trans-TramadolYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2050 g (4.95 mole) (1S, 2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate from step 2 were dissolved in 4000 ml water and treated with 900 g crushed ice. 1000 ml of 36-38 % (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 2500 ml dichloromethane, and was extracted with a further 500 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 1280 g (99% theoretical) of (1S, 2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup.

Workup

  1. additiontreated with 900 g
  2. customcrushed ice
  3. extractionThe mixture was subsequently extracted with 2500 ml dichloromethane
  4. extractionwas extracted with a further 500 ml dichloromethane
  5. customafter phase separation
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. customAfter removing the solvent
  8. distillationby distillation

Sources & evidence

ORD record
ord-25a37bf119d145cda2596773da8da71c
Source dataset
uspto-grants-1998_03
Patent number
US05728885

Reaction notes

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