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

Participants

Reaction Conditions

Reaction Steps

2-carbamoyl-1-(4-chlorobenzyl)pyrrolidine was dissolved in 1M BH3-THF (9.4 mL) and heated to 70° C. After 16 h and 25 h, additional 0.5 equiv. of 1M BH3-THF were added. After 40 h, 1 N aqueous HCl solution (14 mL) was added and the reaction was heated to reflux for 3 h, 3 N aqueous HCl solution (6 mL) was added and the reaction was heated for an additional 3 h. The reaction mixture was cooled to 25° C., basicified with 4 N aqueous NaOH solution and extracted with CH2Cl2 (4×15 mL). Chromatography (SiO2, 8:1:1 PrOH—H2O—NH4OH) afforded 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (1.21 g, 86%)

Provenance & Evidence