Carbonocyanidic acid, methyl ester → HCID 9838701, compound

Participants

Reaction Steps

Tetrahydrofuran (55.5 mL) was added to a flask containing tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (10 g, 0.0444 mol). At −78° C., lithium diisopropylamide (24.4 mL, 0.0488 mol) was added dropwise to the reaction. The reaction was allowed to stir for 1 hr, then methyl cyanoformate (4.226 mL, 0.05326 mol) was added dropwise at −78° C. The reaction was let to stir for 5 hrs at room temperature. The reaction was quenched using saturated ammonium chloride solution. Some of the tetrahydrofuran was removed in vacuo. The remaining THF and ammonium chloride mixture was extracted using ethyl acetate three times. The combined ethyl acetate layers were washed with water and dried over sodium sulfate. The solution was filtered, was concentrated, and was purified using flash chromatography (0-100% ethyl acetate in hexane). A yellow oil was recovered (88% yield).

Provenance & Evidence