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

(R)-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/PrOH (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, 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)+.

1. extractionIt was then extracted with CHCl3/PrOH (v. 10:1, 3×200 mL)
2. washwashed with brine (50 mL)
3. dry with materialdried over MgSO4
4. customThe drying agents were removed by filtration
5. concentrationthe filtrates was concentrated under reduced pressure

ORD record

ord-150f077aeea24fc897003c56d91edef5

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241773B2