Cesium carbonate → (R)-3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine

HRID 1384981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384981
S([O:11][CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[Br:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24](O)=[C:23]([CH3:29])[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([O:11][CH2:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]2)=[C:23]([CH3:29])[CH:22]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 15895222(R)-3-tosyloxymethyl-1-methylpiperidine

Produkt 1

HCID 15895221(R)-3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Alternatively, a solution of (R)-3-tosyloxymethyl-1-methylpiperidine (100 mg, 0.35 mmol), 4-bromo-2,6-dimethylphenol (75 mg, 0.37 mmol), and cesium carbonate (240 mg, 0.74 mmol) in dimethylformamide (4 mL) was heated to 65° C. under a nitrogen atmosphere for 1.5 hours. The solution was cooled to room temperature and partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was removed and the aqueous phase extracted once more with ethyl acetate (30 mL). The combined acetate layers were dried over magnesium sulfate and concentrated to afford the (R)-3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine as a clear oil. This material was identical to that prepared in Example 2E when analyzed by chiral HPLC (Chiralpak AD, 97:3:0.1 hexane/2-propanol/diethylamine).

Aufarbeitung

  1. custompartitioned between ethyl acetate (50 mL) and water (30 mL)
  2. customThe organic layer was removed
  3. extractionthe aqueous phase extracted once more with ethyl acetate (30 mL)
  4. dry with materialThe combined acetate layers were dried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-941510ecbb8446a9a50af150ac7c45c4
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262078B1

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