反应详情

To a solution of 3-aminoquinuclidine dihydrochloride (8.0 g, 40.0 mmol) in EtOH (100 mL) was added excess Na2CO3 and the mixture was stirred for 1 h and then filtered. To this solution was added benzaidehyde (3.2 g, 30.0 mmol) and the reaction was stirred at room temperature for 2 h and then NaBH4 (3 pellets, 0.4 g ea.) was added and the reaction was stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue was partitioned between 10% Na2CO3 and EtOAc. The organic layer was separated, dried over K2CO3, filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (92/8 CHCl3/1.0 M NH3 in MeOH) to give N-phenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (4.2 g, 76%) as an intermediate, a pale yellow oil. MH+=217. 1H NMR (CDCl3) 1.4 (m, 3H), 1.7 (m, 1H), 1.9 (m, 2H), 2.45 (2m, 1H), 2.8 (m, 5H), 3.2 (m, 1H), 3.75 (d, 2H), 7.3 (m, 5H).

1. filtrationfiltered
2. stirringthe reaction was stirred at room temperature for 2 h
3. stirringthe reaction was stirred overnight at room temperature
4. customThe solvent was evaporated in vacuo
5. customthe residue was partitioned between 10% Na2CO3 and EtOAc
6. customThe organic layer was separated
7. dry with materialdried over K2CO3
8. filtrationfiltered
9. customthe solvent was evaporated in vacuo
10. customThe residue was chromatographed on silica (92/8 CHCl3/1.0 M NH3 in MeOH)