Lithium hydroxide, monohydrate → HCID 44125115, compound

HRID 601800Notes

Reaction equation

HRID 601800 reaction equation
[CH2:1]([CH:5]1[C:12]2[CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[NH:9][C:8]=2[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].O.[OH-].[Li+]>>[CH2:1]([CH:5]1[C:12]2[CH:11]=[C:10]([C:13]([OH:15])=[O:14])[NH:9][C:8]=2[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180147HCID 59180147, compound

Product 1

HCID 44125115HCID 44125115, compoundYield 63%

Procedure

The title compound was synthesized from methyl 4-isobutyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (37 mg, 0.17 mmol) and lithium hydroxide monohydrate (28 mg, 0.67 mmol) according to General Procedure 7. The crude product was dried onto Silica gel and was purified by flash chromatography (0-80% EtOAc/Heptane) to give 4-isobutyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (11) as a light yellow solid (22 mg, 63%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.94 (d, J=6.62 Hz, 3H), 0.98 (d, J=6.59 Hz, 3H), 1.23-1.32 (m, 1H), 1.40-1.48 (m, 1H), 1.73-1.84 (m, 1H), 1.89-2.01 (m, 1H), 2.53-2.76 (m, 3H), 2.95-3.05 (m, 1H), 6.59 (s, 1H); LCMS-MS (ESI−) 206.2 (M−H); HPLC (UV=100%).

Workup

  1. dry with materialThe crude product was dried onto Silica gel
  2. customwas purified by flash chromatography (0-80% EtOAc/Heptane)

Sources & evidence

ORD record
ord-1335db92e7664efcbe6431416a1ba37e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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