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

HRID 601921Notes

Reaction equation

HRID 601921 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:12]3[NH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].CO>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:12]3[NH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180190Methyl 6-(3-fluorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801706-(3-Fluorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(3-fluorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (116 mg, 0.45 mmol) and lithium hydroxide (188 mg, 4.50 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 mL) was used. The resulting product was purified by chromatography. eluting with heptane-EtOAc, gradient 0 to 50% EtOAc. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.28-2.39 (m, J=12.87, 8.60, 6.35, 6.35 Hz, 1H), 2.64-2.74 (m, 1H), 2.74-2.85 (m, 1H), 2.90-3.01 (m, J=12.83, 8.48, 8.48, 4.32 Hz, 1H), 4.23-4.31 (m, 1H), 6.80-6.87 (m, 2H), 6.89-6.97 (m, 2H), 7.23-7.32 (m, 1H), 8.74 (br. s, 1H). LCMS m/e 246 (M+H). Purity>98% (HPLC).

Workup

  1. customThe resulting product was purified by chromatography
  2. washeluting with heptane-EtOAc, gradient 0 to 50% EtOAc

Sources & evidence

ORD record
ord-5f8aef7055fe4f8ea5eaa275f6cd75fd
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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