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Diethyl Ether → 3-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-8-methyl-8-azabicyclo[3.2.1]octane

HRID 2037113
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2037113
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.[Li]CCCC.[Cl:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:18]=1.CCOCC>C1COCC1>[Cl:16][C:17]1[N:18]=[C:19]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[N:20]=[C:21]([O:10][CH:8]2[CH2:9][CH:3]3[N:2]([CH3:1])[CH:6]([CH2:5][CH2:4]3)[CH2:7]2)[N:22]=1
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Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 178418339Butyllithium

Produkt 1

HCID 872396073-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-8-methyl-8-azabicyclo[3.2.1]octaneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a three neck flask equipped with stirring bar under N2 atmosphere tropine (1 g, 4.24 mmol) was suspended in (anhydrous) THF (15 mL). The mixture was cooled to −78° C. and BuLi (2M in THF) (5.53 ml, 1.2 eq) was added dropwise and the mixture was allowed to warm to 25° C. over minutes. To the reaction mixture 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4.24, mmole) was added and allowed to stir overnight. For work up, ether (100 mL) was added. The organic layer was washed with water (20 mL) and brine (20 mL) and dried over MgSO4. filtered and the solvents were removed to obtain a colorless oil. Further purification by flash-chromatography using CH2Cl2/MeOH/NH3 (15:1:0.1) gave the product as white solid (600 mg, 42% yield); MS (ESI) m/z 340

Aufarbeitung

  1. customIn a three neck flask equipped
  2. temperatureto warm to 25° C. over minutes
  3. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed
  7. customto obtain a colorless oil
  8. customFurther purification by flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-46886be5482242c0976a887453016e9d
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575159B2

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