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

HRID 601852Notes

Reaction equation

HRID 601852 reaction equation
[Cl: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>[Cl: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 59180141Methyl 4-(3-chloro-4-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591800504-(3-Chloro-4-fluorobenzyl)-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-chloro-4-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.034 g, 0.11 mmol) and lithium hydroxide (0.023 g, 0.55 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. 17 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.97-2.16 (m, 1H) 2.44-2.67 (m, 3H) 2.67-2.85 (m, 2H) 3.19-3.29 (m, 1H) 6.31 (s, 1H) 7.10-7.15 (m, 2H) 7.28 (d, J=7.52 Hz, 1H) 19F NMR δ ppm −122.88 (q, J=7.1 Hz); LCMS-MS (ESI−) 292.0 (M−H); HPLC (UV=98.1%), (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-e803d18ab84a4efe8a4993ab10290c88
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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