Diisopropyl diazene-1,2-dicarboxylate → Methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate

HRID 473953

Reaktionsgleichung

Reaktionsgleichung von HRID 473953
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.[Br:11][C:12]1[CH:13]=[CH:14][C:15](O)=[N:16][CH:17]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:1][CH:2]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]2)=[N:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 520596Cyclopentanecarboxylic acid, 3-hydroxy-, methyl esterHCID 178515818HCID 178515818, Verbindung

Produkt 1

HCID 58577907Methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of methyl 3-hydroxycyclopentanecarboxylate A-11 (500.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) was added to a solution of 5-bromopyridin-2-ol (522.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) at room temperature. Diisopropyl azodicarboxylate (1.57 g, 6.00 mmol) was then added dropwise, and the yellow-orange solution was stirred at room temperature for 12 h. The reaction mixture was then quenched with methanol (1.0 mL) and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient) to give methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate A-12 (462.0 mg, Yield=51%). MS (ESI), [M+Na]+ 321, 323.

Aufarbeitung

  1. customThe reaction mixture was then quenched with methanol (1.0 mL)
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9b2e0014adbe449db1634b351e2ff97b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637507B2

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