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

HRID 601932Notes

Reaction equation

HRID 601932 reaction equation
[OH: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>[OH: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 59180152Methyl 6-(3-hydroxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591802376-(3-Hydroxybenzyl)-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-hydroxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (57 mg, 0.21 mmol) and lithium hydroxide (88 mg, 2.10 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. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.04-2.16 (m, 1H) 2.36-2.53 (m, 3H) 2.55-2.64 (m, 1H) 2.96-3.04 (m, 1H) 3.31-3.37 (m, 1H) 6.57 (s, 1H) 6.59-6.67 (m, 3H) 7.04-7.11 (m, 1H). LCMS m/e 258 (M+H). Purity 92% (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-72810cfedcd64ba49f158bf42e6c750a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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