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

HRID 601876Notes

Reaction equation

HRID 601876 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[CH2:9][CH:10]1[C:17]2[CH:16]=[C:15]([C:18]([O:20]C)=[O:19])[NH:14][C:13]=2[CH2:12][CH2:11]1.[OH-].[Li+].CO>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[CH2:9][CH:10]1[C:17]2[CH:16]=[C:15]([C:18]([OH:20])=[O:19])[NH:14][C:13]=2[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180189Methyl 4-(3-(furan-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801954-(3-(Furan-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-(furan-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.024 g, 0.075 mmol) and lithium hydroxide (0.032 g, 0.76 mmol), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1.5 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: 14 mg, 61% yield. LCMS-MS (ESI−) 306.0 (M−H); HPLC (UV=93.7%), (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-20765569762f4e77aa8fa6771e3887f3
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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