反应详情

Ethyl magnesium bromide (15 mL, 1M in diethyl ether, 15 mmol) was added dropwise to a solution of the 1-tert-butyl 3-ethyl piperidine-1,3-dicarboxylate (1.29 g, 5 mmol) in diethyl ether (20 mL) and THF (20 mL) during 10 min. The mixture was stirred for 30 min and thereafter slowly quenched with NH3Cl solution (10 mL, 3M). The phases were separated and the organic phase was evaporated to yield a yellow oil. The oil was dissolved in DCM (2 mL) and TFA (2 mL) was added and the reaction was left for left at room temperature for 15 min at room temperature. The solvents were evaporated and the residue dissolved in EtOAc. HCl was bubbled through the solution in a gentle stream for 10 minutes. The solvent was evaporated and the residue dried in vacuum. Dissolvation in EtOAc (10 mL) and addition of diethyl ether (100 mL) and stirring for 1 h at room temperature gave the title compound as white crystals. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.78-0.91 (m, 6 H) 1.27-1.56 (m, 5 H) 1.83 (d, J=13.18 Hz, 1 H) 1.87-1.98 (m, 2 H) 2.02-2.18 (m, 2 H) 2.65-2.91 (m, 2 H) 3.39 (d, J=12.45 Hz, 1 H) 3.53 (d, J=12.70 Hz, 1 H) 9.22 (s, 1 H) 9.49 (s, 1 H).

1. customslowly quenched with NH3Cl solution (10 mL, 3M)
2. customThe phases were separated
3. customthe organic phase was evaporated
4. customto yield a yellow oil
5. waitthe reaction was left
6. waitfor left at room temperature for 15 min at room temperature
7. customThe solvents were evaporated
8. dissolutionthe residue dissolved in EtOAc
9. customHCl was bubbled through the solution in a gentle stream for 10 minutes
10. customThe solvent was evaporated
11. customthe residue dried in vacuum
12. dissolutionDissolvation in EtOAc (10 mL)
13. additionaddition of diethyl ether (100 mL)
14. stirringstirring for 1 h at room temperature