Cesium carbonate → 3-[(S)-(4-chlorophenyl)(3-hydroxyazetidin-1-yl)methyl]benzonitrile

HRID 1724173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724173
Cl[CH2:2][CH:3]([OH:22])[CH2:4][NH:5][C@@H:6]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@H:6]([N:5]2[CH2:4][CH:3]([OH:22])[CH2:2]2)[C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 670553403-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile

Produkt 1

HCID 576121723-[(S)-(4-chlorophenyl)(3-hydroxyazetidin-1-yl)methyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A solution of 8.0 g (24.0 mmole) of 3-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile and 11.7 g (36 mmole) of Cs2CO3 in 50 mL of dry CH3CN was divided between two 80 mL microwave tubes. The tubes were irradiated in a microwave oven (with cooling) at 160° C. for 8 h. The samples were filtered and the solids were washed with 20 mL of CH3CN and then 20 mL of CH2Cl2. The combined filtrates were concentrated and the residue was portioned between 300 mL ethyl acetate and 100 mL water. The layers were separated and the aqueous layer was washed with 100 mL ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 10-20% ethyl acetate in CH2Cl2 to afford the title compound as a clear oil; 1H-NMR(CDCl3) δ 1.6 (s, 2H, br), 5.24 (s, 1H), 7.24-7.78 (m, 8H) 2.89 (m, 2H), 3.54 (m, 2H), 4.39 (s, 1H), 4.52 (m, 1H), 7.27-7.8 (m, 8H).

Aufarbeitung

  1. customThe tubes were irradiated in a microwave oven
  2. filtrationThe samples were filtered
  3. washthe solids were washed with 20 mL of CH3CN
  4. concentrationThe combined filtrates were concentrated
  5. customThe layers were separated
  6. washthe aqueous layer was washed with 100 mL ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6bb5fd08b3d141448f9063948c9d0aaa
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485732B2

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