Lithium hydroxide, monohydrate → 1H,4H,5H,6H-cyclopenta[b]pyrrole-2-carboxylic acid

HRID 601789Notes

Reaction equation

HRID 601789 reaction equation
C([O:3][C:4]([C:6]1[NH:10][C:9]2[CH2:11][CH2:12][CH2:13][C:8]=2[CH:7]=1)=[O:5])C.O.[OH-].[Li+]>>[NH:10]1[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]2[CH2:13][CH2:12][CH2:11][C:9]1=2

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15319183Ethyl 1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 248605561H,4H,5H,6H-cyclopenta[b]pyrrole-2-carboxylic acidYield 73%

Procedure

The title compound was synthesized from the above ethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (100 mg, 0.56 mmol) using lithium hydroxide monohydrate (94 mg, 2.23 mmol) as the base according to General Procedure 7. The crude product was purified by flash chromatography (0-100% EtOAc/heptane) to give 61 mg (73%) of 1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-2-carboxylic acid (1). 1H NMR (400 MHz, METHANOL-d) δ ppm 2.35-2.44 (m, 2H), 2.54-2.61 (m, 2H), 2.64-2.72 (m, 2H), 6.59 (s, 1H); LCMS-MS (ESI+) 151.9 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe crude product was purified by flash chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-0550f0eee8674f5f8b1c9be26999ce50
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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