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

HRID 601931Notes

Reaction equation

HRID 601931 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:10]2[NH:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][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:10]2[NH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180169Methyl 6-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591800826-(3-Bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.151 g, 0.45 mmol) and lithium hydroxide (0.193 g, 4.6 mmol in 2 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (4 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: 0.014 g (10% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.03-2.13 (m, 1H), 2.37-2.46 (m, 4H), 2.68 (dd, J1=13.28 Hz, J2=8.88 Hz, 1H), 3.08 (dd, J1=13.52 Hz, J2=4.73 Hz, 1H), 6.56 (s, 1H), 7.10-7.12 (m, 1H), 7.17 (t, J=7.74 Hz, 1H), 7.32-7.35 (m, 2H); LCMS-MS (ESI−) 318.0 (M−H); HPLC (UV=96.26%), (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-31b31dcebef3490da6eb10f1d372278a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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