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

HRID 601832Notes

Reaction equation

HRID 601832 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)/[CH:5]=[C:6]1\[CH2:7][CH2:8][C:9]2[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:13]\1=2.[OH:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[OH:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[CH:30]=[CH:29][CH:28]=[C:4]([CH2:5][CH:6]3[C:13]4[CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[NH:10][C:9]=4[CH2:8][CH2:7]3)[CH:3]=2)=[CH:34][CH:33]=1.[OH:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[CH:30]=[CH:29][CH:28]=[C:4](/[CH:5]=[C:6]3\[CH2:7][CH2:8][C:9]4[N:10]([S:18]([C:21]5[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=5)(=[O:19])=[O:20])[C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:13]\3=4)[CH:3]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 66873689(E)-methyl 4-(3-bromobenzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 2

HCID 59180093Methyl 4-((4'-hydroxybiphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873504(E)-methyl 4-((4'-hydroxybiphenyl-3-yl)methylene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Procedure

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).

Sources & evidence

ORD record
ord-a162cf26881b48e0b05fdac654f4ab48
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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