Methanol → 4-((4'-(Hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601875Notes

Reaction equation

HRID 601875 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]3[C:23]4[CH:22]=[C:21]([C:24]([O:26]C)=[O:25])[NH:20][C:19]=4[CH2:18][CH2:17]3)[CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Li+].CO>C1COCC1>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]3[C:23]4[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[NH:20][C:19]=4[CH2:18][CH2:17]3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180154Methyl 4-((4'-(hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591800524-((4'-(Hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-((4′-(hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.012 g, 0.033 mmol) and lithium hydroxide (0.016 g, 0.38 mmol in 0.5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound: 4.5 mg, 39% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.10-2.18 (m, 1H), 2.52-2.63 (m, 3H), 2.79-2.91 (m, 2H), 3.33 (d, J=1.61 Hz, 1H), 4.64 (s, 2H), 6.39 (s, 1H), 7.19 (s, 1H), 7.34 (s, 2H), 7.42 (s, 3H), 7.56 (d, J=8.30 Hz, 2H); LCMS-MS (ESI−) 346.2 (M−H); HPLC (UV=93.1%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH

Sources & evidence

ORD record
ord-bdcd6e3da563458caa856eebc333cb29
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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