HCID 67253499, compound → HCID 58292671, compound

Participants

Reaction Steps

A mixture of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.22 g, 2.82 mmol) and 10% Pd/C (1.0 g) in EtOH (20 mL) was hydrogenated at 40 psi for 30 minutes. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hexane:EtOAc 50:50) to give [1-hydroxy-6-(3-hydroxy-phenoxy)-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.65 g, 68%). 1H NMR (400 MHz, DMSO): δ 7.13 (t, J=8.4 Hz, 1H), 7.06 (d, J=2.4 Hz, 1H), 6.95 (d, J=1.6 Hz, 1H), 6.50 (dd, J=1.6, 8.0 Hz, 1H), 6.38 (dd, J=1.6, 8.0 Hz, 1H), 6.32 (t, J=2.4 Hz, 1H), 5.48 (dd, J=2.4 Hz, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.09 (dd, J=2.4 Hz, 1H), 2.29-2.23 (m, 1H), 2.26 (s, 3H), 1.12 (t, J=4.4 Hz, 3H). MS (ESI) m/z=341 [M−H]−.

Provenance & Evidence