(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate → (r)-5-Tert-butyl-1-((tetrahydrofuran-2-yl)methyl)pyridin-2(1h)-imine

HRID 536727

Reaktionsgleichung

Reaktionsgleichung von HRID 536727
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O[CH2:23][C@H:24]2[CH2:28][CH2:27][CH2:26][O:25]2)(=O)=O)=CC=1>[I-].C([N+](CC)(CC)CC)C.CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8](=[NH:11])[N:9]([CH2:23][C@H:24]2[CH2:28][CH2:27][CH2:26][O:25]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 205879625-Tert-butylpyridin-2-amine

Produkt 1

HCID 66643182(r)-5-Tert-butyl-1-((tetrahydrofuran-2-yl)methyl)pyridin-2(1h)-imine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6225Tetraethylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of Example 59B (0.5 g, 3.3 mmol), (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (0.9 g, 3.6 mmol), and tetraethylammonium iodide (0.4 g, 1.6 mmol) in N,N-dimethylformamide (1.0 mL) was heated at 95° C. for 16 hours. After cooling to ambient temperature, the mixture was quenched with saturated NaHCO3 (10 mL) and extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. LCMS (APCI+) m/z 235 (M+H)+.

Aufarbeitung

  1. customthe mixture was quenched with saturated NaHCO3 (10 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-196510cd32ed4181a98e140955a074e4
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859596B2

Verknüpfte Notizen

Wird geladen…