Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate → Methyl 2,4-dimethyl-3-pyrrolepropionate
Reaktionsgleichung
C(OC([C:11]1[NH:15][C:14]([CH3:16])=[C:13]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:12]=1[CH3:23])=O)C1C=CC=CC=1>CC(C)=O.[Pd]>[CH3:22][O:21][C:19]([CH2:18][CH2:17][C:13]1[C:12]([CH3:23])=[CH:11][NH:15][C:14]=1[CH3:16])=[O:20]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate (3.1 g, 9.8 mmol) was dissolved in acetone (100 mL). This solution was added with 10% Pd—C, and stirred at room temperature under hydrogen gas. When the starting material disappeared, the reaction mixture was filtered, and the filtrate was distilled under reduced pressure. The residue was added with trifluoroacetic acid (10 mL), and heated at 40° C. for 10 minutes under an argon flow. The reaction mixture was added with chloroform, and washed once with water, and the aqueous layer was extracted twice with chloroform. The organic phases were combined, washed once with aqueous Na2CO3 and once with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: CH2Cl2) to obtain the target compound as brown liquid (1.6 g, yield: 90%).