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

HRID 601860Notes

Reaction equation

HRID 601860 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1.[OH-].[Li+].CO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180131HCID 59180131, compound

Product 1

HCID 591801614-(3-Methoxybenzyl)-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-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (116 mg, 0.40 mmol) and lithium hydroxide (167 mg, 4.00 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 to afford the title compound. 74, mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.09-2.18 (m, 1H), 2.53-2.65 (m, 1H), 2.65-2.73 (m, 2H), 2.74-2.85 (m, 2H), 3.28-3.37 (m, 1H), 3.81 (s, 3H), 6.56 (d, J=1.46 Hz, 1H), 6.73-6.83 (m, 3H), 7.22 (t, J=7.81 Hz, 1H), 8.85 (br. s, 1H). LCMS m/e 272 (M+H). Purity 99% (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-ea7dabb2752941649117c4f4c590f103
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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