Ethanol → (betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

To a solution of the above amine (6.85 g, 81.5 mmol) in EtOH (150 mL) heated to 100° C. was added a solution of the above piperidone salt (32.9 g, 122 mmol) in H2O (150 mL) dropwise. The resulting solution was stirred at reflux for 1 hour and then slowly cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with saturated aqueous NaHCO3 (120 mL) and extracted with CH2Cl2 (4×150 mL). The combined organic extracts were washed with H2O (150 mL) and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to give (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile as an orange liquid (11.74 g, 87%). 1H NMR (CDCl3) δ 1.22 (d, 3H, J=6.0 Hz), 2.38-2.59 (m, 6H), 2.82-2.83 (m, 4H), 3.20-3.27 (m, 1H).

1. temperatureat reflux for 1 hour
2. concentrationThe mixture was concentrated under reduced pressure
3. additiondiluted with saturated aqueous NaHCO3 (120 mL)
4. extractionextracted with CH2Cl2 (4×150 mL)
5. washThe combined organic extracts were washed with H2O (150 mL)
6. dry with materialthe organic layer was dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-60553a38d83745c482264a34963f3c82

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491735B2