Dichloromethane → 1-Acetyl-3-Aminopyrrolidine

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.

1. customthe solvent removed under reduced pressure
2. dissolutionThe residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1)
3. stirringstirred for 60 hours
4. filtrationfiltered
5. customsolvent removed from the filtrate under reduced pressure
6. customThe residue was purified by silica gel flash chromatography column
7. washeluting firstly with CHCl3—cC6H12—MeOH (85-14-1, 1.0 1)
8. washto elute the

ORD record

ord-f242749d01864d4b81167f54ba3a3a81

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163928B2