Sodium Iodide → (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

4-Dimethylaminophenethyl tosylate (1.91 g, 6.0 mmol), sodium carbonate (750 mg, 7.0 mmol) and sodium iodide (40 mg, 0.26 mmol) were added to a solution of (R)-3-hydroxypyrrolidine (522 mg, 6.0 mmol) in acetonitrile (40 ml), and they were heated under reflux at 90° C. for 4 hours. The solvent was evaporated under reduced pressure. The obtained residue was distributed in 2 M NaOH and chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane, then with dichloromethane and methanol (50:1) and finally with a mixture of the same solvents (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine in the form of a light yellow oil (1.00 g, 71%).

Provenance & Evidence