Ethyl formate → (1R,3S,5R)-2-(methoxyimino)-6,6-dimethylbicyclo[3.1.1]heptane-3-carbaldehyde

Temperature

-78 °C

To a cold (−78° C.) solution of (1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oxime, 77a, (1.27 g, 7.59 mmol) in THF (33 mL) was added dropwise a solution of n-butyllithium (3.34 mL of 2.5 M solution in hexanes, 8.35 mmol). After stirring the mixture 20 min at −78° C. ethyl formate (0.61 mL, 7.59 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 3 hours and then quenched by pouring into aqueous saturated NaHCO3 solution. The mixture was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (0-20% EtOAc/Hexanes gradient) to afford 810 mg yellow oil: LCMS RT=3.54 (M+H) 196.28.

1. additionwas added dropwise
2. customquenched
3. additionby pouring into aqueous saturated NaHCO3 solution
4. extractionThe mixture was extracted with EtOAc
5. dry with materialThe organic phase was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified via silica gel chromatography (0-20% EtOAc/Hexanes gradient)

ORD record

ord-77afc3b2c3cf4840aaeeed174c635354

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829007B2