4-(Hydroxymethyl)benzeneboronic acid → Methyl 4-((4'-(hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

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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-(hydroxymethyl)phenylboronic acid (0.141 g, 0.93 mmol) according to General Procedure 9.1 to give (E)-methyl 4-((4′-(hydroxymethyl)biphenyl-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′-(hydroxymethyl)biphenyl-3-yl)methylene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate. Hydrogenation of (E)-methyl 4-((4′-(hydroxymethyl)biphenyl-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 2.10-2.20 (m, 1H), 2.51-2.60 (m, 1H), 2.61-2.68 (m, 2H), 2.87 (dd, J=7.25, 2.03 Hz, 2H), 3.35 (quin, J=6.88 Hz, 1H), 3.71 (s, 3H), 4.20 (br. s, 1H), 4.67 (s, 2H), 6.35-6.37 (m, 1H), 7.23 (d, J=7.76 Hz, 1H), 7.35-7.40 (m, 1H), 7.42-7.46 (m, 2H), 7.47-7.51 (m, 2H) 7.59-7.63 (m, 2H), 10.48 (br. s, 1H); LCMS-MS (ESI+) 384.0 (M+Na).

Provenance & Evidence