Hydrochloric Acid → 4-(4-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601849
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[N:11](S(C4C=CC(C)=CC=4)(=O)=O)[C:10]=3[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[Li+].[OH-].Cl>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:29][CH:30]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14797Potassium HydroxideHCID 59180148Methyl 4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Produkt 1

HCID 591801514-(4-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The title compound was synthesized from methyl 4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate in two steps. First, the starting material's methyl ester was hydrolyzed according to General Procedure 7. In this case, 0.070 g (0.274 mmol) of starting ester and potassium hydroxide (10 M, 0.16 mL, 1.6 mmol) were used. The deprotected methyl ester (4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid) (0.035 g, 0.13 mmol) was then dissolved in THF (3 mL) and MeOH (3 mL), and LiOH (0.055 g, 1.3 mmol) in H2O (3 mL) was added and the reaction stirred at 70° C. for 6 h. The reaction was diluted in 25 mL H2O and acidified to pH 2-3 with 1 N HCl, then extracted with 2×50 mL EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 16 mg. 19F NMR δ ppm −102.42 (m, J=5.4) LCMS-MS (ESI−) 258.0 (M−H); HPLC (UV=98.52%), (ELSD=100%).

Aufarbeitung

  1. extractionextracted with 2×50 mL EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography (Isco CombiFlash)
  5. washeluting with a gradient of 0-100% EtOAc/heptane

Quellen und Nachweise

ORD-Eintrag
ord-909a791f00404e01a28d16a7a788dc26
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902252B2

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