(3R)-1-Azabicyclo[2.2.2]octan-3-ol--hydrogen chloride (1/1) → 3-Quinuclidinol, (-)-

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Reaction Steps

(3R)-3-Quinuclidinol hydrochloride (Aldrich, 20 g, 12.2 mmol) was treated with NaOH aqueous solution (20%, 50 mL) at ambient temperature for 10 min. It was then extracted with CHCl3/iPrOH (v. 10:1, 3×200 mL). The extracts were combine, washed with brine (50 mL) and dried over MgSO4. The drying agents were removed by filtration and the filtrates was concentrated under reduced pressure to give the title compound as white solid (15.5 g, yield, 99%). 1H NMR (300 MHz, CD3OD) δ 1.36–1.50 (m, 1H), 1.52–1.60 (m, 1H), 1.76–1.85 (m, 2H), 1.90–2.05 (m, 1H), 2.50–2.95 (m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82–3.88 (m, 1H) ppm. MS (DCl/NH3): m/z 128 (M+H)+.

Provenance & Evidence