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

(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)+.

1. extractionextracted with CHCl3/i-PrOH (10:1, 3×200 mL)
2. washwashed with brine (50 mL)
3. dry with materialdried over MgSO4
4. customAfter removal of the drying agents
5. filtrationby filtration
6. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-6511b64780a54009815a074a5dddf948

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365193B2