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

HRID 601933Notes

Reaction equation

HRID 601933 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:11]2[NH:12][C:13]([C:15]([O:17]C)=[O:16])=[CH:14][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:11]2[NH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:10]=2[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180168Methyl 6-(3-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801946-(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 6-(3-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (127 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. 80 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.10-2.21 (m, 1H) 2.53-2.76 (m, 4H) 2.91-2.99 (m, 1H) 3.34-3.44 (m, 1H) 3.82 (s, 3H) 6.72-6.77 (m, 2H) 6.78-6.86 (m, 2H) 7.24-7.31 (m, 2H) 8.28 (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-b26a492f55b5445481858a83c6f99e54
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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