反应详情

Methyl magnesium bromide (5 mL, 3M 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 at room temperature for 15 min. 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. Dissolution in EtOAc (100 mL) and stirring for 1 h at room temperature yielded the solid product, which was filtered off and dried in vacuum to produce white crystals. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.01 (d, J=15.87 Hz, 6 H) 1.08-1.26 (m, 1 H) 1.46-1.68 (m, 2 H) 1.74 (d, J=10.99 Hz, 2 H) 2.47-2.56 (m, 1 H) 2.55-2.75 (m, 1 H) 3.11 (d, J=12.45 Hz, 1 H) 3.24 (d, J=12.45 Hz, 1 H) 8.81 (s, 1 H) 9.18 (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 at room temperature for 15 min
6. customThe solvents were evaporated
7. dissolutionthe residue dissolved in EtOAc
8. customHCl was bubbled through the solution in a gentle stream for 10 minutes
9. customThe solvent was evaporated
10. customthe residue dried in vacuum
11. dissolutionDissolution in EtOAc (100 mL)
12. stirringstirring for 1 h at room temperature
13. customyielded the solid product, which
14. filtrationwas filtered off
15. customdried in vacuum
16. customto produce white crystals