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

HRID 601884Notes

Reaction equation

HRID 601884 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19]C)=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.O.[OH-].[Li+].C1COCC1>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([OH:19])=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59180128Methyl 4-(3,5-dimethylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591800854-(3,5-Dimethylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3,5-dimethylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (150 mg, 0.45 mmol) and lithium hydroxide monohydrate (108 mg, 4.5 mmol), according to General Procedure 7. A 1:1 mixture of THF and methanol (10 mL) was used. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to give the title compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.16-2.22 (m, 1H), 2.24 (s, 6H), 2.66-2.92 (m, 3H), 4.08 (t, J=7.35 Hz, 1H), 6.51 (s, 1H), 6.78 (s, 2H), 6.80 (s, 1H). LCMS m/e 256 (M+H) and 95% pure by HPLC.

Workup

  1. customThe resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min)

Sources & evidence

ORD record
ord-710279fb67c7400698473779ddb746af
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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