Lithium hydroxide, monohydrate → HCID 44125253, compound

HRID 601893Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:19][C:11]2[NH:12][C:13]([C:15]([O:17]C)=[O:16])=[CH:14][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>>[CH2:1]([CH:8]1[CH2:19][C:11]2[NH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 168937Lithium hydroxide, monohydrate

HCID 59180046HCID 59180046, compound

Product 1

HCID 44125253HCID 44125253, compoundYield 39%

Procedure

The title compound was synthesized from methyl 5-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.017 g, 0.065 mmol) and lithium hydroxide monohydrate (0.019 g, 0.45 mmol) according to General Procedure 7. The crude product was purified by reverse phase HPLC (40-100% MeOH: water, 0.1% formic acid), to give 5-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (23) as a light brown solid (6.1 mg, 39%). Rf (1:1 EtOAc:heptane)=0.12; 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.30-2.49 (m, 2H), 2.62-2.90 (m, 4H), 3.08-3.20 (m, 1H), 6.57 (s, 1H), 7.16-7.30 (m, 5H); LCMS-MS (ESI+) 242.3 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

customThe crude product was purified by reverse phase HPLC (40-100% MeOH: water, 0.1% formic acid)

Sources & evidence

ORD record: ord-ce240483e7584ab089e9b1d2ca3fd3a3
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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