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

Participants

Reaction Steps

A suspension of 83 (8.0 g, 17.41 mmol) and 10% Pd/C (3.6 g) in MeOH (240 mL) was subjected 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, 90:9:1 CHCl3/CH3OH/NH4OH) to afford amine 95 (3.2 g, 56%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 7.64 (d, J=6.3 Hz, 1H), 7.60 (s, 1H), 7.55 (s, 1H), 7.30 (d, J=1.5 Hz, 1H), 7.15 (s, 1H), 7.03 (dd, J=8.9 Hz, 2.3 Hz, 1H), 2.76 (t, J=7.4 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 1.79-1.69 (m, 2H), 1.59-1.49 (m, 2H), 1.04 (s, 9H), 0.25 (s, 6H).

Provenance & Evidence