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

Temperature

65 °C

(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).

1. temperaturecooled to room temperature
2. customThe organic layer was separated
3. extractionthe aqueous layer extracted with toluene (3×100 mL)
4. washThe combined organic layers were washed with water (3×100 mL), brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-0dd116e57e3444f48806e8d507fcdc22

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07226931B2