1-Naphthalenemethanamine → HCID 18660163, compound

Participants

Reaction Steps

To a slurry of 1-naphthylmethylamine (5.84 g, 37.2 mmol), crushed 3A molecular sieves (10 g), and N-t-butoxycarbonyl-isoleucinal (8.0 g, 37.2 mmol) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (15.8 g, 74.3 mmol) at 0° C. The reaction was allowed to warm slowly to RT and stirred for 48 hrs. The reaction was cooled to 0° C. and quenched with sat. aq. NaHCO3 and stirred for 30 min. The organic layer was separated, washed with saturated brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to provide the title compound as an oil.

Provenance & Evidence