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

Participants

Reaction Conditions

Reaction Steps

(S)-Methanesulfonic acid 1-benzyl-pyrrolidin-3-yl ester (28 g, 110 mmol) was dissolved in anhydrous acetonitrile (60 mL) and solid tetrabutylammonium cyanide (59 g, 220 mmol) was added at once at room temperature. The resulting mixture was heated at 65° C. for 16 h and cooled to room temperature. Saturated NaHCO3 (100 mL) solution was added. The organic layer was separated and the aqueous layer extracted with toluene (3×100 mL). The combined organic layers were washed with water (3×100 mL), brine, and dried over Na2SO4 and concentrated under reduced pressure to give (R)-1-benzyl-3-cyanopyrrolidine as brown oil (21 g), which was vacuum distilled at 150° C./5 mmHg to give a colorless liquid (19 g, 85%): [α]23−22.0° (c=2.5, MeOH); 1H NMR (400 MHz, CDCl3) δ 7.36-7.17 (m, 5H), 3.66 (app s, 2H), 3.05-2.99 (m, 1H), 2.93 (app t, J=8.8 Hz, 1H), 2.72-2.60 (m, 3H), 2.31-2.22 (m, 1H), 2.17-2.11 (m, 1H).

Provenance & Evidence