反应详情

To a magnetically stirred suspension of [4-(3-cyclopentylidenemethyl-4-methoxy-phenyl)piperidin-1-yl]-oxo-acetic acid (1.2 mmol, 0.40 g) in dry toluene (15 mL) at room temperature was added oxalyl chloride (2.0M in CH2Cl2 ; 1.3 mmol, 0.65 mL) dropwise over 10 minutes, followed by DMF (3 drops) to promote gas evolution. The resulting homogeneous solution stirred at room temperature for 45 minutes, at which time saturated NH3 /CH3CN (15 mL) was added dropwise over 15 minutes. A white solid precipitated out of solution as the mixture was stirred for another 3/4 hour. At that time, TLC analysis shows reaction to be complete. The solution was diluted with H2O to dissolve the white precipitate and then the THF was removed in vacuo. The aqueous phase was diluted with saturated aqueous NaHCO3 solution (100 mL) and then extracted with EtOAc (2×200 mL). Each organic phase was washed with H2O (1×100 mL) and then the combined organics were dried (Na2SO4) and concentrated to yield a white solid. This compound was purified via column chromatography (SiO2 : 40% EtOAc/hex) to afford a pure white solid of the title compound as a pure white solid, mp 116°-117° C. (0.7 mmol, 0.231 g, 56%).

1. additionwas added dropwise over 15 minutes
2. customA white solid precipitated out of solution as the mixture
3. customreaction
4. dissolutionto dissolve the white precipitate
5. customthe THF was removed in vacuo
6. additionThe aqueous phase was diluted with saturated aqueous NaHCO3 solution (100 mL)
7. extractionextracted with EtOAc (2×200 mL)
8. washEach organic phase was washed with H2O (1×100 mL)
9. dry with materialthe combined organics were dried (Na2SO4)
10. concentrationconcentrated
11. customto yield a white solid
12. customThis compound was purified via column chromatography (SiO2 : 40% EtOAc/hex)