Carbon Dioxide → HCID 59495804, Verbindung

HRID 400749

Reaktionsgleichung

Reaktionsgleichung von HRID 400749
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH3:19])=[C:9]([CH2:20][O:21][CH3:22])[CH:8]=1.[C:23](=[O:25])=[O:24]>CCOCC.CCOCC.CCOC(C)=O.O>[CH3:22][O:21][CH2:20][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:23]([OH:25])=[O:24]

Komponenten

7

Edukt 3

HCID 280Carbon DioxideHCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidineHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 59495804HCID 59495804, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 21584169Diethylether ethylacetateLösungsmittel

Versuchsvorschrift

To anhydrous Et2O (130 mL) at −78° C. was added tert-butyllithium (63.79 mL; 1.50 M; 95.68 mmol) (solution in pentane) which was followed by the slow addition of a solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine obtained in step 3 (12.97 g; 43.49 mmol) in anhydrous Et2O (20 mL). After 40 min, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min after which time it was diluted with Et2O/EtOAc (1:1), water (pH 4-5). The organic layers were combined, dried over MgSO4 and the solvents were removed under reduced pressure to give a yellow oil that was triturated in iPr2O and pentane, filtered off and washed with pentane to give the title compound as a beige powder. 1H NMR (CDCl3, 300 MHz) δ 8.22 (d, J=2.1 Hz, 1H), 8.00 (dd, J=8.3, 2.1 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 4.60 (d, J=12.3 Hz, 1H), 4.55 (d, J=12.3 Hz, 1H), 3.46 (s, 3H), 3.17 (m, 1H), 3.02 (m, 1H), 2.63 (m, 1H), 1.88-1.65 (m, 4H), 1.55-1.40 (m, 2H), 0.88 (d, J=6.2 Hz, 3H). LC/MS (Method B): 264.1 (M+H)+.

Aufarbeitung

  1. dry with materialdried over MgSO4
  2. customthe solvents were removed under reduced pressure
  3. customto give a yellow oil that
  4. customwas triturated in iPr2O
  5. filtrationpentane, filtered off
  6. washwashed with pentane

Quellen und Nachweise

ORD-Eintrag
ord-ae1ead1750264a5592ce7d31955bbf06
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741923B2

Verknüpfte Notizen

Wird geladen…