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

HRID 601856Notes

Reaction equation

HRID 601856 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[NH:10][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:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180250Methyl 4-(3-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591802244-(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 4-(3-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (261 mg, 0.90 mmol) and lithium hydroxide (188 mg, 4.50 mmol in 3 mL H2O), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 50% EtOAc to afford the title compound. 147 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.06-2.17 (m, 1H) 2.53-2.64 (m, 1H) 2.64-2.73 (m, 2H) 2.73-2.85 (m, 2H) 3.26-3.36 (m, 1H) 6.52 (d, J=1.32 Hz, 1H) 7.08 (dt, 1H) 7.19-7.26 (m, 3H) 8.87 (br. s, 1H). LCMS m/e 276 (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-f20f60b7bc314758930702f661670723
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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