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

HRID 1963268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963268
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:31])[O:29][CH3:30]>C(Cl)Cl.C(Cl)(=O)OC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]2[C:28]([O:29][CH3:30])=[O:31])=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731633HCID 66731633, Verbindung

Produkt 1

HCID 66735290Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6586Methyl chloroformateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2-(4-fluorobenzyl)piperidine-4-carboxylate (4.981 g, 19.82 mmol) was dissolved in DCM (150 mL) and DIPEA (4.14 mL, 23.79 mmol), then methyl carbonochloridate (1.873 mL, 23.79 mmol) was added. The solution was stirred at room temperature for 50 min. More methyl carbonochloridate (a few drops) were added and the reaction continued at room temperature for 1 h. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate (5.82 g, 95%) as a yellow oil. MS m/z 310 (M+H)+

Aufarbeitung

  1. waitthe reaction continued at room temperature for 1 h
  2. washThe reaction mixture was washed with 0.1 M HCl
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e4c0eaf21e74859b736c37e41ad6eb0
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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