Reaktion #2846

Reaktionsgleichung

(2-oxo-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester

4-bromomethyl-thiophene-2-carbonitrile

sodium hydride

→

title compound

Ausbeute 86.3%

[1-(5-Cyanothiophene-3-ylmethyl)-2-oxo-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester

Ausbeute 86.3%

Lösungsmittel

THF DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturto warm to ambient temperatures
3. 3
   Sonstigethe solution is quenched by the addition of sat. NH4Cl
4. 4
   workup.ADDITIONThe solution is diluted with H2O and EtOAc
5. 5
   SonstigeThe layers are separated
6. 6
   WaschenThe organic layer is washed with H2O and sat. NaCl
7. 7
   TrocknenThe organic layer is dried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe crude product is purified by column chromatography
11. 11
    Wascheneluting with gradient of 20% EtOAc/CH2 Cl2 to 30% EtOAc/CH2Cl2

Vorschrift

To a solution of (2-oxo-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester (3.2 g, 16 mmol), prepared as described in EXAMPLE 1, Part A in 80 mL of THF:DMF (10:1) at 0° C. is added 4-bromomethyl-thiophene-2-carbonitrile (3.23 g, 16 mmol) and sodium hydride (60% dispersion in oil, 0.67 g, 16.8 mmol). After addition, the solution was allowed to warm to ambient temperatures. After 2 h, the solution is quenched by the addition of sat. NH4Cl. The solution is diluted with H2O and EtOAc. The layers are separated. The organic layer is washed with H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/CH2 Cl2 to 30% EtOAc/CH2Cl2 to afford the title compound (4.0 g, 13.8 mmol) as a white solid.

Quelle