Water → (1S,3R)-3-(3-pyridyl)cyclopentanol

HRID 655164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655164
C([O:4][C@H:5]1[CH2:9][CH2:8][C@@H:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:6]1)(=O)C.[OH-].[Na+].O>CO>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C@@H:7]2[CH2:8][CH2:9][C@H:5]([OH:4])[CH2:6]2)[CH:11]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59486131(1S,3R)-3-(3-pyridyl)cyclopentyl acetate

Produkt 1

HCID 59486133(1S,3R)-3-(3-pyridyl)cyclopentanolAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (1S,3R)-3-(3-pyridyl)cyclopentyl acetate (5.43 g, 26.5 mmol) in MeOH (80 ml) was added 1N NaOH aq. (26 mL) at 4° C., and stirred for 2 h at same temperature. To the reaction mixture was added H2O and then extracted with CH2Cl2 four times, and the combined layers were dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (EtOAc) to yield (1S,3R)-3-(3-pyridyl)cyclopentanol (3.99 g, 92%) as colorless oil.

Aufarbeitung

  1. extractionextracted with CH2Cl2 four times
  2. dry with materialthe combined layers were dried over Na2SO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by column chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-730b8cd6965147809e39876cf5f1b31e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071591B2

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