Hydrogen Peroxide → HCID 69430334, compound

3-(3-Benzyl-8-hydroxy-3-aza-bicyclo[3.2.1]oct-8-yl)-benzonitrile (1.86 g, 5.84 mmol) in DMSO (30 mL) with potassium carbonate (0.121 g, 0.88 mmol) was charged with 30% aqueous hydrogen peroxide (2.98 mL, 29.2 mmol) and allowed to stir at room temperature for 2 h (or until judged complete by TLC). The reaction was cooled in an ice bath then quenched with water (50 mL) causing the product precipitate as white solids. The mixture was acidified to pH 1 with 1N HCl (25 mL) to dissolve the product and the aqueous layer was washed with ether (2×30 mL). The ether extracts were back extracted with water (1×30 mL). The combined acidic aqueous layers were neutralized to pH 8 with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (3×50 mL), washed with 50% saturated aqueous NaCl solution (3×50 mL) then dried by azeotroping with THF (3×100 mL) yielding a white solid (1.69 g, 86%). 1H NMR (400 MHz, CD3OD) δ 7.96 (t, J=1.5 Hz, 1H), 7.95 (d, J=7.9 Hz, 1H), 7.64 (d, J=7.4 Hz, 1H), 7.41–7.15 (m, 6H), 3.56 (br s, 2H), 2.88 (m, 2H), 2.61 (m, 2H), 2.46 (br, s, 2H), 1.76 (m, 2H), 1.35 (m, 2H); APCI MS m/z 337.2 (M+1)+; mp 210–214° C.

1. temperatureThe reaction was cooled in an ice bath
2. customthen quenched with water (50 mL)
3. dissolutionto dissolve the product
4. washthe aqueous layer was washed with ether (2×30 mL)
5. extractionThe ether extracts were back extracted with water (1×30 mL)
6. extractionThe product was extracted with EtOAc (3×50 mL)
7. washwashed with 50% saturated aqueous NaCl solution (3×50 mL)
8. customthen dried
9. customby azeotroping with THF (3×100 mL)

ORD record

ord-72ec4c6520e8452fadd1d2cd7c0afdc6

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241887B2