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

Temperature

-70 °C

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.

1. customat −70° C
2. temperaturethe temperature was slowly raised to 0° C. over a period of 20 min
3. customThe reaction was quenched
4. additionby pouring 4% aqueous H2SO4 (30 mL)
5. extractionextraction with DCM (3×30 mL)
6. washThe combined DCM layers were washed with 30 mL 4% aqueous H2SO4, 20 mL brine twice
7. dry with materialdried over Na2SO4
8. customThe solvent was removed under reduced pressure
9. customthe product isolated by flash column chromatography
10. washeluting with 0% to 50% ethyl acetate/hexane gradient solvent

ORD record

ord-535632488a9546c798781ee3a855b998

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119692B2