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

HRID 601886Notes

Reaction equation

HRID 601886 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.O.[OH-].[Li+].C1COCC1>CO>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:2]=[CH:3][C:4]([CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59180167Methyl 4-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801254-(Biphenyl-4-yl)-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-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (156 mg, 0.49 mmol) and lithium hydroxide monohydrate (83 mg, 1.97 mmol), according to General Procedure 7. A 1:2 mixture of THF and methanol (15 mL) was used. The resulting product was purified by flash chromatography (Isco CombiFlash) eluting with a gradient of 0-80% EtOAc/Heptane to give the title compound: 135 mg, 90.6%. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.22-2.33 (m, 1H), 2.73-2.82 (m, 1H), 2.82-2.91 (m, 1H), 2.91-3.00 (m, 1H), 4.23 (t, J=7.20 Hz, 1H), 6.56 (s, J=1H), 7.24-7.32 (m, 3H) 7.37-7.43 (m, 2H), 7.50-7.55 (m, 2H), 7.57-7.61 (m, 2H); LCMS-MS (ESI+) 304.2 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by flash chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-80% EtOAc/Heptane

Sources & evidence

ORD record
ord-cdfebd790f6a4d459de6e0b516e511bd
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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