反应详情

11-Benzyl-5-Ethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (160 mg, mmol), ammonium formate (220 mg, 3.49 mmol) and 10% Pd(OH)2/C (100 mg) were combined in methanol (MeOH) (5 mL) and warmed to reflux for 15 min. The mixture was cooled, filtered, concentrated, diluted with sat. aq. Na2CO2 soln. and extracted with EtOAc (3×20 mL). The extracts were dried (MgSO4), filtered and concentrated to an oil (94 mg, 83%). (TLC 50% EtOAc/hexanes (NH3) Rf 0.20). 1H NMR (CDCl3) δ 6.90 (d, J=9.0 Hz, 1H). 6.66 (2H), 3.97 (m, 2H), 3.08 (dd, J=18.0, 6.0 Hz, 1H), 2.94 (m, 3H), 2.76-2.65 (3H), 1.96 (m, 2H), 1.88 (d, J=11.0 Hz, 1H), 1.38 (t, J=7.0 Hz, 3H). This material was dissolved in excess 1N HCl MeOH and concentrated. Recrystallization from CH2Cl2/Et2O provided a solid (74 mg, 68%). mp 243-245° C.

1. temperaturewarmed
2. temperatureto reflux for 15 min
3. temperatureThe mixture was cooled
4. filtrationfiltered
5. concentrationconcentrated
6. additiondiluted with sat. aq. Na2CO2 soln
7. extractionand extracted with EtOAc (3×20 mL)
8. dry with materialThe extracts were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated to an oil (94 mg, 83%)
11. dissolutionThis material was dissolved in excess 1N HCl MeOH
12. concentrationconcentrated
13. customRecrystallization from CH2Cl2/Et2O