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

Participants

Reaction Steps

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.

Provenance & Evidence