反应详情

A solution of {(Z)-4-[(R)-2-oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-but-2-enyloxy}-acetic acid methyl ester (24.6 mg, 0.064 mmol) in CH3CN (1.5 mL) was added via cannula to hydrido(triphenylphosphine)copper(I) hexamer (125 mg, 0.064 mmol) at −40° C. After 1 h at −40° C., the reaction was allowed to warm to rt. After 3 h at rt, the reaction was quenched by addition of a solution of NH4OH and saturated aqueous NH4Cl (1:1, 6 mL). The mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (20%→70% EtOAc/CH2Cl2, gradient) afforded 19.6 mg (79%) of the title compound.

1. waitAfter 3 h at rt
2. customthe reaction was quenched by addition of a solution of NH4OH and saturated aqueous NH4Cl (1:1, 6 mL)
3. extractionThe mixture was extracted with EtOAc (3×10 mL)
4. washThe combined organic phase was washed with brine (20 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash column chromatography on silica gel (20%→70% EtOAc/CH2Cl2, gradient)