Triphenylphosphine → 2-[(3S)-1-azabicyclo[2.2.2]octan-3-yloxy]-fluoren-9-one

Participants

Reaction Steps

To a 0° C. mixture of 2-hydroxyfluoren-9-one (196 mg, 1.00 mmol; Aldrich), (3R)-quinuclidin-3-ol (151 mg, 1.20 mmol; Acros), and polymer-bound triphenylphosphine (500 mg, 3 mmol/g; Aldrich) in THF (5 mL) was added diethylazodicarboxylate (200 μL, 1.27 mmol; Aldrich). After 1 h, the reaction mixture was allowed to warm to room temperature and was stirred overnight (16 h). The mixture was filtered through diatomaceous earth, the filter pad rinsed with dichloromethane, and the organic extracts purified twice by flash chromatography (80 g silica gel, eluting with 1-5% of 10% NH4OH/MeOH in CH2Cl2) to afford the title compound (104 mg, 0.340 mmol, 34% yield). MS (DCI/NH3): m/z 306 (M+1)+.

Provenance & Evidence