Acetic Acid → Carbamate

Participants

Reaction Conditions

Reaction Steps

(3S and R,4R and S)-1-Methyl-3-nitro-4-(2-(trifluoromethyl)phenyl) pyrrolidine (296.8 mg, 1.082 mmol) was dissolved in MeOH (5 mL) and the reaction mixture was cooled to 0° C. Acetic acid (5 mL) and zinc (354 mg, 5.41 mmol) were added and the reaction mixture was warmed to room temperature and stirred under N2 for 16 h. The suspension was filtered over Celite and washed with MeOH. The filtrate was concentrated in vacuo, the residue suspended in EtOAc, cooled in an ice bath, and basified with conc. NH4OH. The organic phase was separated, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford (3S and R,4R and S)-1-methyl-4-(2-(trifluoromethyl)phenyl)pyrrolidin-3-amine, which was carried onto the next step without further purification. MS ESI calc'd. For C12H15F3N2 [M+1]+ 245. found 245.

Provenance & Evidence