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

HRID 601929Notes

Reaction equation

HRID 601929 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:10]2[NH:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][C:9]=2[CH2:8][CH2:7]1.[OH-].[Li+].CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:10]2[NH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180204Methyl 6-(3-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591802166-(3-Chlorobenzyl)-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-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (140 mg, 0.48 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. 90 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.07-2.20 (m, 1H) 2.52-2.68 (m, 3H) 2.74-2.82 (m, 1H) 2.86-2.93 (m, 1H) 3.33-3.43 (m, 1H) 6.75 (d, J=1.61 Hz, 1H) 7.03-7.09 (m, 1H) 7.20-7.23 (m, 1H) 7.25-7.29 (m, 2H) 8.35 (br. s., 1H). LCMS m/e 276 (M+H). Purity>75% (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-4fa9bb2ed7d2447db6925f20a2ba7134
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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