Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → HCID 58975237, compound

Participants

Reaction Steps

To a solution of N-carbethoxy-4-tropinone (1-1) (8.00 g, 40.6 mmol, Acros) and (methoxymethyl)tripheylphosphonium chloride (16.7 g, 48.7 mmol) in THF was added sodium bis(trimethylsilyl)amide (48.7 mL, 48.7 mmol, 1.0 N in THF) at 0° C. After stirring at room temperature overnight, the solvent was removed by rotary evaporation. The mixture was quenched with a saturated aqueous solution of NH4Cl, extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-20% ethyl acetate/hexanes as eluent) afforded (1-2) as a colorless oil.

Provenance & Evidence