1-Naphthaldehyde → N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester

Participants

Reaction Steps

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]glycine methyl ester (2.00 g, 6.97 mmol) was dissolved in 1,2-dichloroethane (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 (Na2SO4), 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.

Provenance & Evidence