Benzylamine → HCID 86755475, compound

Participants

Reaction Steps

Acetic acid (12.5 ml) was added to a stirred mixture of 2-oxo-1,2,3,4-tetrahydronaphthalene-3-acetic acid methyl ester (3.62 g, 17 mmol), and benzylamine (7.2 ml, 66 mmol) in a 1:1 mixture of tetrahydrofuran and methanol (120 ml) at 0° C. under argon. After 0.5 h, sodium cyanoborohydride (2.09 g, 33 mmol) was added and the resultant mixture stirred at room temperature. After 16 h, aqueous 10% sodium hdyroxide was added and the solvent evaporated in vacuo. The residue was partitioned between water (100 ml) and dichloromethane (2×200 ml). The combined extracts were washed with water (100 ml), brine (100 ml), then dried (Na2SO4) and evaporated in vacuo to give a brown solid (4.38 g). Chromatography on silica using 0-5% methanol-ethyl acetate gradient elution afforded the title compound as a yellow solid (1.75 g, 38%).

Provenance & Evidence