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

HRID 601874Notes

Reaction equation

HRID 601874 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]3[C:22]4[CH:21]=[C:20]([C:23]([O:25]C)=[O:24])[NH:19][C:18]=4[CH2:17][CH2:16]3)[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].CO>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]3[C:22]4[CH:21]=[C:20]([C:23]([OH:25])=[O:24])[NH:19][C:18]=4[CH2:17][CH2:16]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180093Methyl 4-((4'-hydroxybiphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801204-((4'-Hydroxybiphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-((4′-hydroxybiphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.044 g, 0.13 mmol) and lithium hydroxide (0.055 g, 1.31 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 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 a light pink solid: 21.7 mg, 51% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.13 (s, 1H), 2.48-2.62 (m, 3H), 2.80 (dd, J=7.05, 3.78 Hz, 2H), 3.25-3.29 (m, 1H), 6.39 (s, 1H), 6.81-6.86 (m, 2H), 7.09 (d, J=7.52 Hz, 1H), 7.25-7.30 (m, 2H), 7.33-7.37 (m, 1H), 7.38-7.42 (m, 2H); LCMS ESI− 332.2 (M−H); HPLC (UV=98.1%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH
  3. customwater (with 0.1% formic acid) to afford a light pink solid

Sources & evidence

ORD record
ord-5e563902af5b491f8801a0301d6705bf
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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