Carbon Dioxide → HCID 59495804, Verbindung

HRID 1630970

Reaktionsgleichung

Reaktionsgleichung von HRID 1630970
C([Li])(C)(C)C.CCCCC.Br[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[CH3:24])=[C:14]([CH2:25][O:26][CH3:27])[CH:13]=1.[C:28](=[O:30])=[O:29]>CCOCC.CCOCC.CCOC(C)=O>[CH3:27][O:26][CH2:25][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH3:24])[C:28]([OH:30])=[O:29]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 8003PentaneHCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidineHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 59495804HCID 59495804, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 21584169Diethylether ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 1.5M solution of tert-butyllithium in pentane (64 mL, 95 mmol) was added into anhydrous Et2O (130 mL) cooled at −78° C. A solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine (13.0 g, 43.5 mmol) in anhydrous Et2O (20 mL) was added slowly. After 40 minutes, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min. The mixture was diluted with Et2O/EtOAc (1:1, 800 mL) and washed with water (200 mL, pH=4-5 adjusted with a 5N aqueous solution of HCl). The aqueous layer was extracted with EtOAc (400 mL). The organic layers were combined, dried (MgSO4) and the solvents were removed under reduced pressure to give a yellow oil, which was triturated in iPr2O (˜20 mL) and pentane (˜20 mL). The precipitate was filtered off, washed with pentane and dried under reduced pressure to give the title compound as a beige powder. HPLC (Method A), Rt: 1.6 min (purity: 93.5%). UPLC/MS, M+(ESI): 264.2, M−(ESI): 262.2. 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).

Aufarbeitung

  1. washwashed with water (200 mL, pH=4-5
  2. extractionThe aqueous layer was extracted with EtOAc (400 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed under reduced pressure
  5. customto give a yellow oil, which
  6. customwas triturated in iPr2O (˜20 mL)
  7. filtrationThe precipitate was filtered off
  8. washwashed with pentane
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6240eaa076604fc698913272cbcc3ae9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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