Acetonitrile → (R)-1-Benzyl-3-pyrrolidinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

(S)-1-Benzyl-3-mesyloxypyrrolidine (264.3 g, 1.03 mol) was dissolved in acetonitrile (170 mL) and tetrabutylammonium cyanide (556 g, 2.07 mol) was added. The resulting mixture was heated at 65° C. for 2 days and then cooled to room temperature and saturated NaHCO3 (500 mL) added. The organic layer was separated and the aqueous layer extracted with toluene (600 mL and 400 mL). The combined organic layers were washed with water (4×500 mL) and concentrated under reduced pressure to give (R)-1-benzyl-3-cyanopyrrolidine as a brown oil (165 g, 85.6%): IR: 2239 cm-1 ; VPC: 97.0%; 1HNMR (CDCl3, 200 MHz): δ2.0-2.4 (m, 2H), 2.6-2.8 (m, 3H), 2.85-3.10 (m, 2H), 3.65 (s, 2H), 7.3 (m, 5H).

Provenance & Evidence