3-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one → 3-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

Temperature

65 °C

To a solution of 3-carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one (1.45 g) in THF (15 mL) was added 1.0 N BH3 in THF (25 mL). The reaction mixture was stirred at 65° C. for 15 h. After cooling to room temperature, the solvent was removed under reduced pressure. Water (30 mL) and conc. HCl (10 mL) were added and the mixture was stirred at 100° C. for 2 h and room temperature for 1 h. 2 N NaOH aqueous solution (100 mL) was added and the mixture was extracted with AcOEt (50 mL×3). The combined organic layers were dried over K2Co3, filtered and concentrated. Column chromatography (SiO2, 15% CH3OH-5%. Et3N in CH2Cl2) afforded 3-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (860 mg, 19%) as a colorless oil.

1. temperatureAfter cooling to room temperature
2. customthe solvent was removed under reduced pressure
3. additionWater (30 mL) and conc. HCl (10 mL) were added
4. stirringthe mixture was stirred at 100° C. for 2 h and room temperature for 1 h
5. addition2 N NaOH aqueous solution (100 mL) was added
6. extractionthe mixture was extracted with AcOEt (50 mL×3)
7. customThe combined organic layers were dried over K2Co3
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-caf8b1df0bc74fd28ce9c53527799e6f

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362177B1