反应详情

N-[2 (S)-(t-Butoxycarbonylamino)-3 (S)-methylpentyl] glycine methyl ester (2.00 g, 6.97 mmol) was dissolved in 1,2dichloroethane (56 ml) and 3A molecular sieves were added followed by 1-naphthaldehyde (1.89 ml, 13.9 mmol) and sodium triacetoxyborohydride (6.65 g, 31.4 mmol). The mixture was stirred at ambient temperature for 16 h, filtered and evaporated in vacuo. The residue was partitioned between EtOAc (100 ml) and sat. aq. NaHCO3 (25 ml). The aqueous layer was extracted with EtOAc (3×50 ml). The organic extracts were combined, dried (Na2 SO4), filtered, and evaporated in vacuo to afford a residue which was purified by chromatography (SiO2, 15-33% ethyl acetate in hexanes) to afford the title compound as an oil.

1. filtrationfiltered
2. customevaporated in vacuo
3. customThe residue was partitioned between EtOAc (100 ml) and sat. aq. NaHCO3 (25 ml)
4. extractionThe aqueous layer was extracted with EtOAc (3×50 ml)
5. customdried (Na2 SO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford a residue which
9. customwas purified by chromatography (SiO2, 15-33% ethyl acetate in hexanes)