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

HRID 601854Notes

Reaction equation

HRID 601854 reaction equation
[F: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>[F: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 59180099Methyl 4-(3-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801344-(3-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-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.075 g, 0.274 mmol) and lithium hydroxide (0.053 g, 1.37 mmol in 3 mL water), 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: 30 mg, 42% yield. 1H NMR (400 MHz, METHANOL-d) δ ppm 2.05-2.15 (m, 1H), 2.50-2.60 (m, 1H), 2.60-2.65 (m, 2H), 2.75-2.85 (m, 2H), 3.21-3.28 (m, 1H), 6.30 (s, 1H), 6.85-6.95 (m, 2H), 7.00-7.05 (d, 1H), 7.25-7.35 (q, 1H); 19F NMR δ ppm (m, −116.7); LCMS-MS (ESI−) 258.0 (M−H); HPLC (UV=100%), (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-7d9daaef6d754072b048783eca610ac2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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