Diisobutylaluminum hydride → tert-Butyl (3R)-3-formylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence