Lithium hydroxide, monohydrate → 4-(3-Phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601808Notes

Reaction equation

HRID 601808 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:17]3[CH:16]=[C:15]([C:18]([O:20]C)=[O:19])[NH:14][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:17]3[CH:16]=[C:15]([C:18]([OH:20])=[O:19])[NH:14][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66873002Methyl 4-(3-phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 441252474-(3-Phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 57.1%

Procedure

The title compound was synthesized from methyl 4-(3-phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (210 mg, 0.74 mmol) and lithium hydroxide monohydrate (124 mg, 2.96 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-(3-phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (36) as a light brown solid (113.8 mg, 57%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.42-1.59 (m, 2H), 1.64-1.84 (m, 2H), 1.90-2.01 (m, 1H), 2.52-2.75 (m, 5H), 2.88-2.97 (m, 1H), 6.61 (s, 1H), 7.10-7.20 (m, 3H), 7.21-7.28 (m, 2H); LCMS-MS (ESI+) 270.1 (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-62f0f7a1fd964957bbcc67a4ad2f73e7
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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