4-Hydroxyphenylboronic acid → Methyl 4-((4'-hydroxybiphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Participants

Reaction Steps

The title compound was synthesized in three steps. First, (E)-methyl 4-(3-bromobenzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.301 g, 0.62 mmol) was coupled with 4-hydroxyphenylboronic acid (0.129 g, 0.94 mmol) according to General Procedure 9.1 to give (E)-methyl 4-((4′-hydroxybiphenyl-3-yl)methylene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, then tosyl deprotection according to General Procedure 10.1 to give (E)-methyl 4-((4′-hydroxybiphenyl-3-yl)methylene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate. Hydrogenation of (E)-methyl 4-((4′-hydroxybiphenyl-3-yl)methylene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate according to General Procedure 6 (with 5% Pd/C), provided the title compound, which was used without purification in the next step. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.08-2.18 (m, 1H), 2.49-2.60 (m, 1H), 2.60-2.68 (m, 2H), 2.84 (d, J=7.27 Hz, 2H), 3.33 (d, J=6.93 Hz, 1H), 3.70-3.73 (m, 3H), 6.37 (d, J=1.81 Hz, 1H), 6.89-6.95 (m, 2H), 7.15 (d, J=7.66 Hz, 1H), 7.30-7.36 (m, 1H), 7.40-7.45 (m, 2H), 7.46-7.51 (m, 2H), 10.47 (br. s, 1H). LCMS ESI− 346.2 (M−H).

Provenance & Evidence