Methyl iodide → (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

HRID 2244695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244695
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4].[CH3:13]I>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][CH3:13])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 68685924(1SR,3RS,4SR)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester

Produkt 1

HCID 68686720(1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (1SR,3RS,4SR)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester (878 mg; example 15A) in THF (15 ml) was transferred to a sealed tube and treated with Ag2O (3.6 g) and methyl iodide (3.23 ml) and stirred at 60° C. overnight. The reaction mixture was filtered, and the cake was rinsed with plenty of THF. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester (600 mg) as light yellow oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe cake was rinsed with plenty of THF
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35)

Quellen und Nachweise

ORD-Eintrag
ord-0a7b556cfdc34e6f85ae4435ca046022
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678917B2

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