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-Eintrag

ord-60553a38d83745c482264a34963f3c82

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07491735B2