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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence