反应详情

The crude product of 4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine (0.49 g, 2.4 mmole) (Intermediate 9) was dissolved in N,N-dimethylformamide (10 mL) at 0° C., and the resulting solution treated with 2-[N-methyl-N-(tert-butoxycarbonyl)-amino]-3-phenyl-propionic acid (0.73 g, 2.6 mmole) in a minimal amount of DMF, DAEC (0.50 g, 2.6 mmole), HOBT (0.42 g, 3.1 mmole) and NMM (0.40 mL, 3.6 mmole). The mixture was stirred overnight, and was diluted with water (50 mL) and EtOAc (50 mL). The layers were separated and the organic layer was washed with HCl (1N), saturated NaHCO3, and the combined aqueous washings were extracted three times with EtOAc (3×25 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford (R)-{1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester as a yellow oil.

1. customThe layers were separated
2. washthe organic layer was washed with HCl (1N), saturated NaHCO3
3. extractionthe combined aqueous washings were extracted three times with EtOAc (3×25 mL)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. concentrationconcentrated