Triphenylphosphine → (R)-methyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

(R)-methyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoate Dissolved 1,6-naphthyridin-5(6H)-one (10.6 g, 73 mmol), (S)-methyl 2-hydroxypropanoate (8.6 ml, 91 mmol) and triphenylphosphine (30 g, 116 mmol) in 144 mL THF (0.5M) and cooled to 0° C. Then added DEAD (17 ml, 109 mmol) dropwise, monitoring temperature so as not to exceed 5° C. Then let warm to room temperature over 1 hr, where reaction was complete by LCMS. The reaction was concentrated on silica and purified via MPLC, first with a gradient of Hexanes:EtOAc (removes most of PPh3O); then gradient of 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield (R)-methyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoate (16 g, 95% yield) where the ee was confirmed to be >95%.

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