Phenyl isocyanate → N-Phenylcarbamic Acid (3S)-1-azabicyclo[2.2.2]octan-3-yl Ester

A solution of (3S)-(+)-quinuclidin-3-ol (0.50 g, 3.93 mmol) [M. Langlois, C. Meyer, and J. L. Soulier, Synth. Comm., 23, 1895-1911 (1992)], phenyl isocyanate (0.47 mL, 4.32 mmol, 1.1 equivalents), and dibutyltin dilaurate (0.013 mL, 0.08 mmol) in anhydrous toluene (20 mL) was heated at reflux under nitrogen for 1 hour. The resulting reaction mixture was evaporated under reduced pressure, and the resulting solid was placed in 1N HCl (25 mL). The resulting aqueous mixture was extracted with ethyl acetate (2×25 mL), basified to pH 10 with Na2CO3, and extracted with chloroform (3×50 mL). The chloroform extracts were combined, dried (MgSO4), and evaporated under reduced pressure. The resulting solid was recrystallized using toluene (5 mL) to afford the title compound (0.875 g, 90%) as a white solid: mp 129.0-130.0° C.; FAB LRMS m /z (relative intensity, %) 247 (MH+, 39), 110 (100); [α]22D =-7.5° (c=1.0, MeOH).

1. temperatureat reflux under nitrogen for 1 hour
2. customThe resulting reaction mixture
3. customwas evaporated under reduced pressure
4. extractionThe resulting aqueous mixture was extracted with ethyl acetate (2×25 mL)
5. extractionextracted with chloroform (3×50 mL)
6. dry with materialdried (MgSO4)
7. customevaporated under reduced pressure
8. customThe resulting solid was recrystallized

ORD record

ord-6e7836553f1d4913a5a5f3c719f7e0c8

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998429