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

HRID 601859Notes

Reaction equation

HRID 601859 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1.[OH-].[Li+].CO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180244Methyl 4-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591800764-(3-Bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.099 g, 0.30 mmol, 1 equiv) and lithium hydroxide (0.124 g, 2.96 mmol), 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 the title compound: 37 mg, 39% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.03-2.11 (m, 1H), 2.48-2.57 (m, 1H), 2.60-2.64 (m, 2H), 2.75 (dd, J1=7.32 Hz, J2=3.71 Hz, 2H), 3.21-3.28 (m, 1H), 6.31 (s, 1H), 7.14-7.20 (m, 2H), 7.32-7.35 (m, 2H); LCMS-MS (ESI−) 318.0 (M−H); HPLC (UV=98.99%), (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-8ae2c2e318224fbbbf05c5f5195db939
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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