Methyl chloroformate → Dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylate

HRID 1963171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963171
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]1[C:29]([O:30][CH3:31])=[O:32]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731925Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride

Produkt 1

HCID 66734584Dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride (2.34 g, 8.02 mmol) was dissolved in DCM (50 mL), then DIPEA (3.50 mL, 20.05 mmol) was added. Methyl carbonochloridate (0.884 mL, 11.23 mmol) was added dropwise to the solution. The mixture was stirred at room temperature for 4 h, washed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL), then dried through a phase-separator and evaporated yielding dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylate (2.38 g, 95%) as an orange oil.

Aufarbeitung

  1. washwashed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase-separator
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-64288e0017a94c4980df06aa7cc1d94f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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