Ammonium formate → HCID 11298276, compound

Temperature

110 °C

To a mixture of 3-imidazol-1-yl-1-azabicyclo[2.2.2]oct-2-ene (1a) (356 mg, 2.03 mmol) and ammonium formate (2.6 g, 40.6 mmol) in absolute EtOH (6 mL) was added 10% Pd/C (178 mg, 50% w/w). The sealed reaction vessel was heated to 110° C. for 13 hrs before cooling to ambient temperature. The mixture was filtered through diatomaceous earth (0.75″ by 2″ diameter), washed liberally with EtOH and concentrated to a white-yellow tacky residue which was subsequently purified by flash chromatography (SiO2—40 grams; gradient elution: 5-30% 3N NH3/MeOH—EtOAc at 60 mL/min over 25 min) to yield the title compound (188 mg, 52%). Mass spectrum (ES+): M+1: 178 (100%); 1H NMR (300 MHz, CDCl3) δ 1.50 (m, 1H), 1.64 (m, 1H), 1.77 (m, 2H), 2.09 (app q, J=3 Hz, 1H), 2.81-3.05 (m, 4H), 3.15 (dd, J=14.5, 4.4 Hz, 1H), 3.47 (ddd, J=14.5, 9.7, 1.8 Hz, 1H), 4.26 (m, 1H), 7.05 (s, 1H), 7.08 (s, 1H), 7.62 (s, 1H).

1. customThe sealed reaction vessel
2. temperaturebefore cooling to ambient temperature
3. filtrationThe mixture was filtered through diatomaceous earth (0.75″ by 2″ diameter),
4. washwashed liberally with EtOH
5. concentrationconcentrated to a white-yellow tacky residue which
6. customwas subsequently purified by flash chromatography (SiO2—40 grams; gradient elution: 5-30% 3N NH3/MeOH—EtOAc at 60 mL/min over 25 min)

ORD record

ord-255492355b2741798cc33ec82b05978f

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384954B2