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

HRID 601850Notes

Reaction equation

HRID 601850 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[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>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[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 59180111Methyl 4-(3,4-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801394-(3,4-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-(3,4-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.10 g, 0.34 mmol) and lithium hydroxide (0.143 g, 3.4 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. 46 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.99-2.16 (m, 1H), 2.45-2.68 (m, 3H), 2.68-2.86 (m, 2H), 3.17-3.29 (m, 1H), 6.30 (s, 1H), 6.97 (ddd, J=6.36, 4.19, 2.05 Hz, 1H), 7.02-7.21 (m, 2H). 19F NMR δ ppm −141.99 (m), −145.62 (m); LCMS-MS (ESI−) 276.0 (M−H); HPLC (UV=98.41%), (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-a4f888ddb8ea4b61a3cd03b7cc0a300f
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…