Lithium Hydroxide → 4-(3-Cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601885Notes

Reaction equation

HRID 601885 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19]C)=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Li+].C1COCC1>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([OH:19])=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59180053Methyl 4-(3-cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591802014-(3-Cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3-cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.021 g, 0.079 mmol) and lithium hydroxide (0.035 g, 0.83 mmol), according to General Procedure 7. A 1:1 mixture of THF and methanol (2 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-80% MeOH: water (with 0.1% formic acid) to afford a light pink solid: 8.8 mg (44% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.21 (dd, J=6.35, 2.34 Hz, 1H), 2.79 (s, 2H), 2.91-3.02 (m, 1H), 4.26 (s, 1H), 6.52 (s, 1H), 7.42-7.48 (m, 1H), 7.49-7.56 (m, 3H); LCMS (ESI−) 251.2 (M−H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-80% MeOH
  3. customwater (with 0.1% formic acid) to afford a light pink solid

Sources & evidence

ORD record
ord-6e76c7dae87844e498e4ef98fbfa876b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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