Trifluoroacetic acid → 4-[(Cyclopropyloxy)methyl]piperidine

To a solution of 2.0 g of tert-butyl 4-[(cyclopropyloxy)methyl]piperidine-1-carboxylate in 20 mL of dichloromethane was added 3.0 mL of trifluoroacetic acid, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and then the aqueous layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (chloroform/methanol) to obtain 756 mg of 4-[(cyclopropyloxy)methyl]piperidine.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionto the residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
3. customthe aqueous layer was separated
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by basic silica gel column chromatography (chloroform/methanol)

ORD record

ord-72974516ebbc4ed798d741834e8fb5e2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822448B2