Cesium carbonate → HCID 178490342, Verbindung

HRID 228338

Reaktionsgleichung

Reaktionsgleichung von HRID 228338
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>CN(C=O)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][NH:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]2)=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 875134-(2-Chloroethyl)phenyl methyl etherHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 178490342HCID 178490342, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Heat a mixture of (±)-(trans)-4-aminocyclohexanol (607 m, 5.3 mmol), Cs2CO3 (4.300 g, 13.2 mmol), and 1-(2-chloroethyl)-4-methoxybenzene (0.8 mL) in DMF (10 mL) at 100° C. for 19 hours. Quench the reaction with saturated aqueous NH4Cl (40 mL). Adjust the pH to alkaline and concentrate to dryness. Suspend the residue in 50:40:10 EtOAc/CH2Cl2/2.0 M NH3 in MeOH and stir vigorously for 1 hour. Decant the supernatant. Suspend the residue in 10:90 2.0 M NH3 in MeOH/CH2Cl2 for 30 minutes and filter. Combine the organic layers, concentrate, and purify by flash chromatography, eluting with 75:15:10 EtOAc/CH2Cl2/2.0 M NH3 in MeOH to afford the title compound (258.3 mg, 20%): MS ES+ 250.0 (M+H)+, HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=1.96 min, 100% purity.

Aufarbeitung

  1. temperatureHeat
  2. customQuench
  3. customthe reaction with saturated aqueous NH4Cl (40 mL)
  4. concentrationconcentrate to dryness
  5. customDecant the supernatant
  6. customfor 30 minutes
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify by flash chromatography
  10. washeluting with 75:15:10 EtOAc/CH2Cl2/2.0 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-69d60fac8bd94c89a22b159bdbd24ae4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

Verknüpfte Notizen

Wird geladen…