1-Naphthaleneboronic acid → (S)-methyl 2-(naphthalen-1-ylamino)propanoate

Participants

Reaction Steps

To a dry round bottom flask equipped with a stir bar was added L-alanine methyl ester hydrochloride (500 mg, 3.58 mmol), 1-Naphthalene boronic acid (1000 mg, 5.81 mmol), dry Cu(OAc)2 (715 mg, 3.93 mmol), 4 A° molecular sieves (1.34 g). The flask was sealed with septum, evacuated and back filled with O2 atmosphere. Triethyl amine (0.92 mL), and dry DCM (30 mL) were added at room temperature, stirred for 48 h. The reaction mixture was quenched with 13 mL 2M NH3 in methanol. The volatiles were removed in vacuo and the resulting crude oil was purified by silica gel flash chromatography ethyl acetate/n-hexane (10:90) to give 280 mg of the title compound as brown viscous oil (34% yield).

Provenance & Evidence