Dichloromethane → 1-Acetyl-3-Aminopyrrolidine

Participants

Reaction Steps

To (3,4-dimethoxy-benzylidene)-pyrrolidin-3-yl-amine (3 mmol) in dry methylene chloride (30 mL) and triethylamine (7.5 mmol) at room temperature was added acetyl chloride (3.5 mmol) dropwise. The mixture was stirred for 6 hours at room temperature, then the solvent removed under reduced pressure. The residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1) and stirred for 60 hours. The solution was neutralized with solid sodium carbonate, filtered, and solvent removed from the filtrate under reduced pressure. The residue was purified by silica gel flash chromatography column, eluting firstly with CHCl3—cC6H12—MeOH (85-14-1, 1.0 1) to elute the faster moving spots, and then with CHCl3—MeOH—NH3/MeOH (93-5-2), to obtain 1-acetyl-3-aminopyrrolidine, a compound of formula (4) as an oil.

Provenance & Evidence