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

HRID 601864Notes

Reaction equation

HRID 601864 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[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.O.[OH-].[Li+].CO>C1COCC1>[CH3:21][C:19]1[CH:18]=[C:4]([CH:3]=[C:2]([CH3:1])[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 168937Lithium hydroxide, monohydrateHCID 59180193Methyl 4-(3,5-dimethylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801744-(3,5-Dimethylbenzyl)-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-(3,5-dimethylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.066 g, 0.23 mmol) and lithium hydroxide monohydrate (0.049 g, 1.16 mmol), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF was used. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to afford the title compound. 30 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.06 (ddt, J=12.47, 8.52, 6.03, 6.03 Hz, 1H), 2.26 (s, 6H), 2.44-2.70 (m, 5H), 3.17-3.26 (m, 1H), 6.31 (s, 1H), 6.79 (s, 2H), 6.82 (s, 1H). LCMS m/e 270 (M+H) and 97% pure by HPLC.

Workup

  1. customThe resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min)

Sources & evidence

ORD record
ord-aef9e95f307b4c88a7f2b6fb2a4d060a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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