Lithium hydroxide, monohydrate → HCID 44125119, compound

HRID 601803Notes

Reaction equation

HRID 601803 reaction equation
[CH2:1]([CH:8]1[C:15]2[CH:14]=[C:13]([C:16]([O:18]C)=[O:17])[NH:12][C:11]=2[CH2:10][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[C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[NH:12][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180191HCID 59180191, compound

Product 1

HCID 44125119HCID 44125119, compoundYield 81%

Procedure

The title compound was synthesized from methyl 4-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (25 mg, 0.098 mmol) and lithium hydroxide monohydrate (25 mg, 0.39 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-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (17) as a light red solid (19 mg, 81%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.05-2.14 (m, 1H), 2.48-2.58 (m, 1H), 2.59-2.66 (m, 2H), 2.74 (dd, J=13.32, 7.81, 1H), 2.79 (dd, J=13.32, 6.98, 1H), 3.22-3.30 (m, 1H), 6.29 (s, 1H), 7.15-7.21 (m, 3H), 7.24-7.29 (m, 2H); LCMS-MS (ESI+) 240.2 (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-8cfa27eb88044a83bac1421e30d09ff3
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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