Acetonitrile → (S)-1-Benzyl-pyrrolidine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

(R)-1-Benzyl-3-mesyloxypyrrolidine (5.0 g, 20 mmol) was dissolved in acetonitrile (6 mL) and tetrabutylammonium cyanide (11.1 g, 41.4 mmol) was added. The mixture was heated at 65° C. for 3 hours and then cooled to room temperature and extracted with ethyl ether (100 mL). The organic layer was washed with saturated NaHCO3 (2×50 mL), dried over MgSO4, and concentrated under reduced pressure to give (S)-1-benzyl-3-cyanopyrrolidine (3.1 g, 85%) as a yellow oil: VPC: 100%; 1HNMR (CDCl3, 60 MHz): δ1.9-2.4 (m, 2H), 2.5-3.1 (m, 5H), 3.60 (s, 2H), 7.30 (s, 5H).

Provenance & Evidence