Methyl 1-Benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate → Methyl 1-benzyl-3-(3-bromo5-methyl-phenyl)piperidine-4-carboxylate

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Reaktionsgleichung

C1COCC1.C1(C)C=CC=CC=1.[Br:13][C:14]1[CH:15]=[C:16]([Mg]Br)[CH:17]=[C:18]([CH3:20])[CH:19]=1.[CH2:23]([N:30]1[CH2:35][CH:34]=[C:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1C=CC=CC=1>[CH2:23]([N:30]1[CH2:31][CH2:32][CH:33]([C:36]([O:38][CH3:39])=[O:37])[CH:34]([C:16]2[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([Br:13])[CH:15]=2)[CH2:35]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

A 2.5 M THF/toluene solution of (3-bromo-5-methylphenyl)magnesium bromide (40 mL, 99 mmol) was cooled to −15° C., and methyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate (9.85 g, 42.6 mmol) in benzene (17.5 mL) was slowly added for 3 h at −15° C. The reaction mixture was stirred additional 2 h at −15° C. and warmed to 20° C. The reaction was quenched by addition of saturated NH4Cl aqueous solution followed by extraction with EtOAc. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to give methyl 1-benzyl-3-(3-bromo5-methyl-phenyl)piperidine-4-carboxylate (12.2 g, 30.3 mmol).

Aufarbeitung

temperaturewarmed to 20° C
customThe reaction was quenched by addition of saturated NH4Cl aqueous solution
extractionfollowed by extraction with EtOAc
dry with materialThe combined organic solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

Quellen und Nachweise

ORD-Eintrag: ord-bcede513a1d44b43b9027d3e1b14246d
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07795436B2

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