Lithium hydroxide, monohydrate → HCID 44125120, compound

HRID 601798Notes

Reaction equation

HRID 601798 reaction equation
[CH2:1]([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)[CH2:2][CH3:3].O.[OH-].[Li+]>>[CH2:1]([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)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180159HCID 59180159, compound

Product 1

HCID 44125120HCID 44125120, compoundYield 79%

Procedure

The title compound was synthesized from methyl 4-propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (95 mg, 0.46 mmol) and lithium hydroxide monohydrate (77 mg, 1.83 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 70 mg of 4-propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (7) as a light yellow solid (79%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.96 (t, J=7.03 Hz, 3H), 1.36-1.56 (m, 4H), 1.92-2.03 (m, 1H), 2.52-2.76 (m, 3H), 2.87-2.96 (m, 1H), 6.61 (s, 1H); LCMS-MS (ESI−) 192.2 (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-fd92130ebde54966970fee498303cf85
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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