Lithium hydroxide, monohydrate → HCID 44125122, compound

HRID 601806Notes

Reaction equation

HRID 601806 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][CH2:8][CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19]C)=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.[OH-].[Li+]>>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][CH2:8][CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([OH:19])=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180188HCID 59180188, compound

Product 1

HCID 44125122HCID 44125122, compoundYield 63.8%

Procedure

The title compound was synthesized from methyl 4-(4-methoxyphenethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (235 mg, 0.78 mmol) and lithium hydroxide monohydrate (132 mg, 3.14 mmol) according to General Procedure 7. Silica gel was added, the solvent stripped off and the silica gel-imbedded material was purified by flash chromatography (0-80% EtOAc/Heptane) to give 4-(4-methoxyphenethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (34) as a light yellow solid (142 mg, 63%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.64-1.84 (m, 2H), 1.96-2.08 (m, 1H), 2.53-2.78 (m, 5H), 2.85-2.97 (m, 1H), 3.75 (s, 3H), 6.67 (s, 1H), 6.77-6.86 (m, 2H), 7.06-7.16 (m, 2H); LCMS-MS (ESI+) 286.1 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. additionSilica gel was added
  2. customthe silica gel-imbedded material was purified by flash chromatography (0-80% EtOAc/Heptane)

Sources & evidence

ORD record
ord-a2153dfd678647678c5063b2c9610050
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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