Potassium Permanganate → HCID 22958903, compound

Participants

Reaction Steps

A solution of ethyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate (1-3) (1.84 g, 8.71 mmol) in t-BuOH (50.0 mL) was diluted with an aqueous 5% NaH2PO4 solution (35.3 mL, 14.8 mmol, 0.42 N in water). With vigorous stirring, an aqueous 1.0 M KMnO4 solution (52.3 mL, 52.3 mmol) was added at room temperature. The mixture was stirred for 10 minutes and quenched with a saturated aqueous solution of Na2SO3. The resulting pH of the mixture was adjusted to 3 with cold (0° C.) dilute HCl to dissolve the colloidal MnO2. The mixture was then extracted with EtOAc and the combined organic layers were washed with brine, dried over anhydrous MgSO4, concentrated to give (1-4) as white solid.

Provenance & Evidence