Water → Tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate

HRID 69864

Reaktionsgleichung

Reaktionsgleichung von HRID 69864
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].O>C1COCC1>[N+:21]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[O:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])([O-:23])=[O:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 27357814-Chloro-3-nitropyridine

Produkt 1

HCID 69047653Tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled solution (0° C.) of tert-butyl 2-hydroxyethylcarbamate (1.1 eq) in THF, NaH (1.3 eq) was added, stirred for 1 hr, and then 4-chloro-3-nitropyridine (1.0 eq) was added. The reaction mixture was stirred at RT overnight, poured into cold water, and extracted with EtOAc. Organic layer was dried over Na2CO3, filtered, and concentrated to yield tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate. LCMS (m/z): 284.1 (MH+); LC Rt=2.09 min.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT overnight
  2. extractionextracted with EtOAc
  3. dry with materialOrganic layer was dried over Na2CO3
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-afb6c2f3f4194cc7956fbfdf80b47324
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822497B2

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