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

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Reaction Steps

(R)-3-Quinuclidinol hydrochloride (Aldrich, 20 g, 12.2 mmol) was treated with NaOH aqueous solution (20%, 50 mL) at ambient temperature for 10 minutes and extracted with CHCO3/isopropyl alcohol (10:1, 3×200 mL). The extracts were combine, washed with brine (50 mL), dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a white solid (15. 5 g, yield, 99%). 1H NMR (300 MHz, MeOH-d4) 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