Methanol → 6-Propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601920Notes

Reaction equation

HRID 601920 reaction equation
[CH2:1]([CH:4]1[C:8]2[NH:9][C:10]([C:12]([O:14]C)=[O:13])=[CH:11][C:7]=2[CH2:6][CH2:5]1)[CH2:2][CH3:3].O.[OH-].[Li+].CO>C1COCC1>[CH2:1]([CH:4]1[C:8]2[NH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:7]=2[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59180192Methyl 6-propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801536-Propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 53.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.15 g, 0.72 mmol) and lithium hydroxide monohydrate (0.3 g, 7.24 mmol), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (10 mL) was used. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to give the title compound (75 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.94 (t, J=7.0 Hz, 3H) 1.32-1.49 (m, 3H), 1.62-1.80 (m, 1H), 1.93-2.08 (m, 1H), 2.43-2.65 (m, 3H), 3.01 (br. s, 1H) 6.57 (s, 1H). LCMS m/e 249 (M−H) and 96% 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-7d8bc6ca5b0c444e8275d32367373a1e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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