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

HRID 1070724

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(3-Methylsulfanyl-phenyl)-1,2,3,6-tetrahydro-pyridine (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).

Workup

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

Sources & evidence

ORD record: ord-85d033facdfb450397499c0cd669d28f
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903120B2

Linked notes

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