Benzyl 4-[6-(2,3-Dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate → 3-[6-(4-Aminobutyl)naphthalen-2-yloxy]propane-1,2-diol

Participants

Reaction Steps

A suspension of benzyl 4-[6-(2,3-dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate (31, 236 mg, 0.5 mmole) and 10% Pd/C (96 mg) in MeOH (70 mL) was subjected to hydrogenation conditions (1 atm) for 1 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 then concentrated in vacuo to afford diol 32 (123 mg, 78%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.67 (d, J=8.4 Hz, 2H), 7.56 (s, 1H), 7.30 (dd, J=8.4, 1.5 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 7.14 (dd, J=8.7, 2.4 Hz, 1H), 4.18-3.99 (m, 3H), 3.76-3.65 (m, 2H), 2.75 (dt, J=10.8, 7.2 Hz, 4H), 1.80-1.70 (m, 2H), 1.62-1.52 (m, 2H).

Provenance & Evidence