Methyl chloroformate → 4-(3-Methylsulfanyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

HRID 2220096

Reaktionsgleichung

[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.Cl[C:23]([O:25][CH3:26])=[O:24]>C(Cl)Cl>[CH3:26][O:25][C:23]([N:12]1[CH2:11][CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13]1)=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-(3-Methylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine (2 g) and NEt3 (1 g) were dissolved in CH2Cl2 (75 ml) and cooled to 0° C. Methyl chloroformate (0.96 g) dissolved in CH2Cl2 (20 ml) was added dropwise and the reaction mixture was then allowed to reach room temperature. After an additional two hours at room temperature the reaction mixture was washed with 10% Na2CO3 solution, dried (MgSO4), filtered and concentrated by evaporation. The oily residue was chromatographed on a silica column using CH2Cl2:MeOH (19:1 (v/v)) as eluent, 4-(3-methylsulfanyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester (1.4 g). MS m/z (relative intensity, 70 eV) 263 (M+45), 248 (89), 129 (83), 128 (bp), 59 (96).

Aufarbeitung

additionwas added dropwise
customto reach room temperature
washAfter an additional two hours at room temperature the reaction mixture was washed with 10% Na2CO3 solution
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated by evaporation
customThe oily residue was chromatographed on a silica column

Quellen und Nachweise

ORD-Eintrag: ord-4c194305f90046309ed081fb8fb6c1aa
Quelldatensatz: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07417043B2

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