Hydrochloric Acid → 2-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

2-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine was dissolved in 1 M BH3-THF (9.4 mL), and the resulting solution was heated at 70° C. A 1 M BH3-THF (0.5 equivalent) was further added twice after 16 hours and 25 hours. After 40 hours, a 1 M hydrochloric acid was added, and the resulting mixture was refluxed for 3 hours. A 3 M hydrochloric acid (6 mL) was added, and the reaction product was stirred for another 3 hours with heating, then cooled to 25° C., alkalinized with a 6 M aqueous solution of NaOH and extracted with dichloromethane (4×15 mL). The obtained crude product was purified by chromatography (SiO2, PrOH/H2O/NH4OH=8:1:1) to thereby afford 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (1.21 g, 86%).

Provenance & Evidence