Tetrahydrofuran → Methyl 1-benzyl-3-(3-bromophenyl)piperidine-4-carboxylate
Reaktionsgleichung
C1COCC1.[Br:6][C:7]1[CH:8]=[C:9]([Mg]Br)[CH:10]=[CH:11][CH:12]=1.[CH2:15]([N:22]1[CH2:27][CH:26]=[C:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH3:31])=[O:29])[CH:24]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Br:6])[CH:8]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
A 0.5 M THF solution of (3-bromophenyl)magnesium bromide (20 mL, 10 mmol) was cooled to −15° C., and methyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate (1.05 g, 4.3 mmol) in toluene (3.0 mL) was slowly added for 3 h at −15° C. The reaction mixture was warmed to 20° C. and 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-bromophenyl)piperidine-4-carboxylate (1.0 g, 2.6 mmol).
Aufarbeitung
- customquenched 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-15c39f80fdea4bae98202778e2fd0952
- Quelldatensatz
- uspto-grants-2010_09
- Patentnummer
- US07795436B2
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