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

HRID 601851Notes

Reaction equation

HRID 601851 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]1[C:12]2[CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[NH:9][C:8]=2[CH2:7][CH2:6]1.[OH-].[Li+].CO>C1COCC1>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]1[C:12]2[CH:11]=[C:10]([C:13]([OH:15])=[O:14])[NH:9][C:8]=2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180239Methyl 4-(2,4-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591802234-(2,4-Difluorobenzyl)-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-(2,4-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.062 g, 0.213 mmol) and lithium hydroxide (0.045 g, 1.07 mmol), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 41 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.12 (m, 1H), 2.56 (m, 1H), 2.65 (m, 2H), 2.78 (d, J=7.37 Hz, 2H), 3.20-3.30 (m, 1H), 6.29 (s, 1H), 6.81-6.95 (m, 2H), 7.22 (m, 1H); 19F NMR δ ppm −116.13 (m), −116.30 (m); LCMS-MS (ESI−) 276.0 (M−H); HPLC (UV=99.0%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-4bcadedad0bc4fed9d9cdb21aeef60dd
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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