Reaktion #1831863

Reaktionsgleichung

Magnesium

product

1-tert-butyl 3-ethyl 4-(4-chlorophenyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

hydrochloric acid

→

title compound

Ausbeute 80.0%

(±)-1-tert-butyl 3-ethyl 4-(4-chloro-phenyl)piperidine-1,3-dicarboxylate

Ausbeute 80.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with ethyl acetate
2. 2
   WaschenThe combined organic extracts were washed with saturated sodium bicarbonate, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–25% ethyl acetate/hexanes as eluent)

Vorschrift

Magnesium metal (1.23 g, 51.0 mmol) was added in three portions over approximately 0.3 h to a stirred solution of the product of step D (1.85 g, 5.1 mmol) in methanol (40 mL) at ambient temperature. After stirring overnight, the reaction mixture was poured into 1 N hydrochloric acid (100 mL) and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–25% ethyl acetate/hexanes as eluent) provided the title compound (mixture of cis/trans diastereoisomers) as a colorless oil (1.5 g).

Quelle