Methyl chloroformate → Dimethyl 2-(3-fluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963272
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][NH:7]1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:31])[O:29][CH3:30]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][N:7]1[C:28]([O:29][CH3:30])=[O:31]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732105Methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate

Produkt 1

HCID 66734612Dimethyl 2-(3-fluorobenzyl)piperidine-1,4-dicarboxylateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate (7.6 g, 30.24 mmol) was dissolved in DCM (200 mL) and DIPEA (6.32 mL, 36.29 mmol), then methyl carbonochloridate (3.3 mL, 41.91 mmol) was added. The solution was stirred at room temperature for 2 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-(3-fluorobenzyl)piperidine-1,4-dicarboxylate (9.30 g, 99%) as a brown oil. MS m/z 310 (M+H)+

Aufarbeitung

  1. washThe reaction mixture was washed with 0.1 M HCl
  2. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-222c1f9fa8df41afbff1653ed5a1dd42
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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