반응 #2846

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

4-bromomethyl-thiophene-2-carbonitrile

sodium hydride

→

title compound

수율 86.3%

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

수율 86.3%

용매

THF DMF

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후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도to warm to ambient temperatures
3. 3
   기타the solution is quenched by the addition of sat. NH4Cl
4. 4
   workup.ADDITIONThe solution is diluted with H2O and EtOAc
5. 5
   기타The layers are separated
6. 6
   세척The organic layer is washed with H2O and sat. NaCl
7. 7
   건조The organic layer is dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The crude product is purified by column chromatography
11. 11
    세척eluting with gradient of 20% EtOAc/CH2 Cl2 to 30% EtOAc/CH2Cl2

실험 절차

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.

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