Lithium hydroxide, monohydrate → HCID 44125114, compound

HRID 601799Notes

Reaction equation

HRID 601799 reaction equation
[CH:1]([CH:4]1[C:11]2[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[NH:8][C:7]=2[CH2:6][CH2:5]1)([CH3:3])[CH3:2].O.[OH-].[Li+]>>[CH:1]([CH:4]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[NH:8][C:7]=2[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10899800HCID 10899800, compound

Product 1

HCID 44125114HCID 44125114, compoundYield 21.7%

Procedure

The title compound was synthesized from methyl 4-isopropyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.09 g, 0.43 mmol) and lithium hydroxide monohydrate (185 mg, 4.3 mmol) according to General Procedure 7. The crude product was dried onto Silica gel and was purified by chromatography (0 to 100% EtOAc/heptane) to give 4-isopropyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (10) as brown solid (0.018 g, 21%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.93 (d, J=2.68 Hz, 3H) 0.95 (d, J=2.68 Hz, 3H) 1.67 (dq, J=13.37, 6.67 Hz, 1H) 2.04-2.14 (m, J=12.81, 8.91, 5.71, 5.71 Hz, 1H) 2.44-2.55 (m, 1H) 2.56-2.80 (m, 3H) 6.63 (s, 1H). LCMS m/e 194 (M+H). 92.0% pure by HPLC.

Workup

  1. dry with materialThe crude product was dried onto Silica gel
  2. customwas purified by chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-66e49a14ae6846f68915c4aebb6657be
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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