(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 (20 g, 12.2 mmol; Aldrich) was treated with aq. NaOH (20%, 50 mL) at ambient temperature for 10 min, then extracted with CHCl3/i-PrOH (10:1, 3×200 mL). The extracts were combined, washed with brine (50 mL) and dried over MgSO4. After removal of the drying agents by filtration, the filtrate was concentrated under reduced pressure to afford the title compound as white solid (15.5 g, 122 mmol, 99% yield). 1H NMR (300 MHz, methanol-d4) δ 3.88-3.82 (1H, m), 3.10 (1H, ddd, J=14, 8, 2 Hz), 2.95-2.50 (5H, m), 2.05-1.90 (1H, m), 1.85-1.76 (2H, m), 1.60-1.52 (1H, m), 1.50-1.36 (1H, m). MS (DCl/NH3): m/z 128 (M+1)+.

Provenance & Evidence