Allyl bromide → 1-tert-Butyl 2-methyl (2S,4R)-4-{[6-(allyloxy)pyridin-2-yl]oxy}pyrrolidine-1,2-dicarboxylate

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Reaction Conditions

Reaction Steps

A 500 mL round bottom flask under nitrogen was charged with the product of Step 4 (4.95 g, 14.63 mmol), tetrahydrofuran (200 ml), allyl bromide (2.53 ml, 29.3 mmol), and cesium carbonate (4.77 g, 14.63 mmol). Heated in a 60° C. oil bath for 18 hours. HPLC/MS o.k. Cooled. Evaporated. Added 2.5% potassium bisulfate. Extracted three times with ethyl acetate, washed combined organic portions with brine, dried with anhydrous magnesium sulfate, filtered and rotary evaporated filtrate. Subjected to flash column chromatography eluting with 70 hexane/30 ethyl acetate. Evaporation of fractions containing product gave the title compound as a pale oil. (4.56 g, 12.05 mmol, 82% yield). LCMS (ES+) m/z 379.3 (M+H)+.

Provenance & Evidence