Lithium hydroxide, monohydrate → 4-(3-Phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid
Reaktionsgleichung
[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]=1Komponenten
3
Versuchsvorschrift
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%).