Lithium hydroxide, monohydrate → 3-(1,1-Dimethylethyl)-1,4,5,6-tetrahydro-4-oxocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601796Notes

Reaction equation

HRID 601796 reaction equation
[C:1]([C:5]1[C:6]2[C:16](=[O:17])[CH2:15][CH2:14][C:7]=2[NH:8][C:9]=1[C:10]([O:12]C)=[O:11])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>>[C:1]([C:5]1[C:6]2[C:16](=[O:17])[CH2:15][CH2:14][C:7]=2[NH:8][C:9]=1[C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180105HCID 59180105, compound

Product 1

HCID 441249833-(1,1-Dimethylethyl)-1,4,5,6-tetrahydro-4-oxocyclopenta[b]pyrrole-2-carboxylic acidYield 37.4%

Procedure

The title compound was synthesized from methyl 3-tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (33 mg, 0.14 mmol) and lithium hydroxide monohydrate (30 mg, 0.71 mmol) according to General Procedure 7. Purification by reverse phase semi-preparative HPLC provided a pure fraction (11.6 mg, 37%) of 3-tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (3). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.46 (s, 9H), 2.82-2.90 (m, 4H); LCMS-MS (ESI+) 221.7 (M−H); HPLC (UV=95.8%).

Workup

  1. customPurification by reverse phase semi-preparative HPLC

Sources & evidence

ORD record
ord-bacdf85a64c1413884bcf3317911f879
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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