Lithium Hydroxide → 3-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid

HRID 1935206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935206
C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 674834933-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 224679003-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acidAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid methyl ester (450 mg, 1.45 mmol) in tetrahydrofuran (5 mL) was treated with a 0.8M aqueous lithium hydroxide solution (2.18 mL, 1.74 mmol). The resulting reaction mixture was stirred at 25° C. for 3 d. The reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by precipitation from methylene chloride/ethyl acetate to afford 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid (271 mg, 63%) as a white solid: mp 136-138° C.; EI-HRMS m/e calcd for C19H21NO2 (M+) 295.1572, found 295.1572.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was purified by precipitation from methylene chloride/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-eb328bd7fcde41d288e7dbf20e7dff55
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384220B2

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