Methyl chloroformate → Dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963311
[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][NH:6]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][N:6]1[C:29]([O:30][CH3:31])=[O:32]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731652HCID 66731652, Verbindung

Produkt 1

HCID 66734456Dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylateAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(2,5-difluorobenzyl)piperidine-4-carboxylate (6.65 g, 24.69 mmol) in DCM (100 mL) and DIPEA (5.16 mL, 29.63 mmol) was added methyl carbonochloridate (2.53 mL, 32.10 mmol) dropwise at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with 0.15 M HCl (250 mL). The organic phase was separated, washed with satd NaHCO3, dried using a phase separator and evaporated to yield dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate (8.1 g, 100%). MS m/z 328 (M+H)+

Aufarbeitung

  1. customThe reaction was quenched with 0.15 M HCl (250 mL)
  2. customThe organic phase was separated
  3. washwashed with satd NaHCO3
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-85bee873ae75481ebb7a13eca800befe
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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