Sodium hydride → HCID 66791198, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil, 4.4 mg, 0.11 mmol) was added to a solution of dimethyl 2-oxo-3-phenylpropylphosphonate (26.5 mg, 0.11 mmol) in THF (0.7 mL) at 0° C. After 1 h at 0° C., the mixture of aldehydes from step 4 above (˜0.10 mmol) in THF (0.5 mL) was added via cannula. The reaction was allowed to warm to room temperature. After 18 h at room temperature, the reaction was quenched with aqueous acetic acid (50%, 5 mL) and extracted with EtOAc (3×5 mL). The combined organic phase was washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (20%→60% EtOAc/CH2Cl2, gradient) followed by preparative thin layer chromatography (silica, 5% MeOH/CH2CI2) afforded 6.8 mg (16%) of 4-{2-[(R)-2-oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-ethylsulfanyl }-butyric acid methyl ester.

Provenance & Evidence