Lithium hydroxide, monohydrate → HCID 44125252, compound

HRID 601892Notes

Reaction equation

HRID 601892 reaction equation
[CH3:1][CH:2]1[CH2:14][C:5]2[NH:6][C:7]([C:9]([O:11]CC)=[O:10])=[CH:8][C:4]=2[CH2:3]1.O.[OH-].[Li+]>>[CH3:1][CH:2]1[CH2:14][C:5]2[NH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66873834HCID 66873834, compound

Product 1

HCID 44125252HCID 44125252, compoundYield 14.1%

Procedure

The title compound was synthesized from ethyl 5-methyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.017 g, 0.09 mmol) and lithium hydroxide monohydrate (0.019 g, 0.45 mmol) according to General Procedure 7. The crude was purified by reverse phase HPLC (50-100% MeOH: water, 0.1% formic acid) to give 5-methyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (22) as a light brown solid (2.1 mg, 14%). Rf (1:1 EtOAc:heptane)=0.12; 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.19 (d, J=6.6, 3H), 2.17-2.20 (m, 1H), 2.26-2.32 (m, 1H), 2.75-2.80 (m, 1H), 2.84-2.90 (m, 2H), 6.56 (s, 1H); LCMS-MS (ESI+) 166.0 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe crude was purified by reverse phase HPLC (50-100% MeOH: water, 0.1% formic acid)

Sources & evidence

ORD record
ord-7422962b71f742be871699b368990add
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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