HCID 57828221, compound → 4-[6-(tert-Butyldimethylsilyloxy)naphthalen-2-yl]butan-1-amine

Participants

Reaction Steps

A suspension of crude 29 (900 mg) and 10% Pd/C (400 mg) in MeOH (50 mL) was subject to hydrogenation conditions (1 atm) for 6 h at room temperature. The reaction mixture was filtered through a plug of diatomaceous earth and the plug was washed with MeOH. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80:18:2 CHCl3/CH3OH/NH4OH) to afford amine 77 (405 mg, 27% over two steps) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.62 (t, J=8.9, 2H), 7.52 (br s, 1H), 7.26 (dd, J=8.4, 1.7 Hz, 1H), 7.15 (d, J=2.2 Hz, 1H), 7.04 (dd, J=8.8, 2.5 Hz, 1H), 3.03-2.37 (br s, 1H), 2.74 (t, J=7.5 Hz, 2H), 1.78-1.65 (m, 2H), 1.58-1.47 (m, 2H), 1.01 (s, 9H), 0.23 (s, 6H).

Provenance & Evidence