Sodium Cyanide → (R)-5-Phenylpyrrolidin-2-one

Temperatur

55 °C

To a stirred solution of ethyl 4(R)-amino-4-phenylbutyrate (515 mg, 2.48 mmol) in 20 mL of anhydrous methanol was added sodium cyanide (25 mg, 0.5 mmol) at room temperature. The reaction mixture was stirred at 55° C. for 4 h, cooled to room temperature, concentrated under reduced pressure. The residue was taken up in methylene chloride, washed with water, brine, dried over anhydrous MgSO4, concentrated to afford 391 mg of product (98% yield) as a colorless crystal, mp 103-105° C. (lit.17 102-104° C.). 1H NMR (CDCl3) δ 1.80-1.95 (m, 1H), 2.27-2.42 (m, 2H), 2.45-2.58 (m, 1H), 4.709 (t, 1H, J=7.2 Hz), 7.22-7.38 (m, 5H), 7.425 (br, 1H); 13C NMR (CDCl3) δ 30.19, 30.93, 57.91, 125.34, 127.46, 128.56, 142.43, 178.85.

1. temperaturecooled to room temperature
2. concentrationconcentrated under reduced pressure
3. washwashed with water, brine
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated

ORD-Eintrag

ord-16a1275be0654ee8bd78f1d40fe4bb8a

Quelldatensatz

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06162417