反应详情

温度

0 °C

Glycine methyl ester hydrochloride (4.41 g, 0.035 mol) was dissolved in 1,2-dichloroethane (50 mL) and DMF (5 mL) and treated with 3A molecular sieves (10 g) and N-t-butoxycarbonyl-isoleucinal (6.3 g, 0.029 mol) with stirring at 0° C. Sodium triacetoxyborohydride (9.27 g, 0.044 mol) was added, and the pH of the mixture was adjusted to 6 with triethylamine (3 mL, 0.022 mol). After stirring for 18 h the mixture was filtered, concentrated to a small volume and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic phase was washed with aqueous saturated NaHCO3 solution, brine, and dried (Na2SO4). Filtration and concentration afforded a residue which was purified by flash chromatography (SiO2, EtOAc:hexane, 1:3) to give the title compound.

1. stirringAfter stirring for 18 h the mixture
2. filtrationwas filtered
3. concentrationconcentrated to a small volume
4. custompartitioned between EtOAc and water
5. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
6. washThe combined organic phase was washed with aqueous saturated NaHCO3 solution, brine
7. dry with materialdried (Na2SO4)
8. filtrationFiltration and concentration
9. customafforded a residue which
10. customwas purified by flash chromatography (SiO2, EtOAc:hexane, 1:3)