Water → (6-Morpholin-4-ylmethyl-pyridin-3-yl)-carbamic acid tert-butyl ester

HRID 85163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85163
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][N:8]=1)(=O)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[O:24]1[CH2:25][CH2:26][N:21]([CH2:6][C:7]2[N:8]=[CH:9][C:10]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:12]=2)[CH2:22][CH2:23]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86653797HCID 86653797, Verbindung

Produkt 1

HCID 67170692(6-Morpholin-4-ylmethyl-pyridin-3-yl)-carbamic acid tert-butyl esterAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture containing (5-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate (114; 1.70 g), morpholine (48; 1.0 g, 11.3 mmol) and K2CO3 (2.30 g, 16.9 mmol) in acetonitrile (30 mL) was stirred at room temperature for 12 h. Water (30 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=1:1 to 1:3) to afford tert-butyl 6-(morpholinomethyl)pyridin-3-ylcarbamate 115 (1.20 g, 71% for two steps).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=1:1 to 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-eb95b38ada9e462484096b119a6879bb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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