Diisobutylaluminum hydride → tert-Butyl (3R)-3-formylpiperidine-1-carboxylate
Reaktionsgleichung
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7](OC)=[O:8])[CH2:2]1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH:7]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2]1)=[O:8]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -70 °C
Versuchsvorschrift
To a solution of (R)-1-tert-butyl 3-methyl piperidine-1,3-dicarboxylate (1.9 g, 7.3 mmol) in 60 mL DCM was slowly added DIBAL-H (22 mL, 1M in cyclohexane, 22 mmol) at −70° C. The mixture was further stirred at −70° C. for 20 min and the temperature was slowly raised to 0° C. over a period of 20 min. The reaction was quenched by pouring 4% aqueous H2SO4 (30 mL) and followed extraction with DCM (3×30 mL). The combined DCM layers were washed with 30 mL 4% aqueous H2SO4, 20 mL brine twice and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by flash column chromatography eluting with 0% to 50% ethyl acetate/hexane gradient solvent to give the title compound, 732 mg, as colorless oil.