Trifluoroacetic acid → HCID 117839617, compound

To a dichloromethane solution (14 mL) of tert-butyl 4-(4-fluorophenyl)-3,4-dihydroxypiperidine-1-carboxylate (1.45 g, 4.66 mmol) synthesized in Reference Synthesis Example 39, trifluoroacetic acid (14 mL) was added and the resultant solution was stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure by 4 mL and saturated sodium bicarbonate aqueous solution was added to the concentrated solution, followed by extraction from the resultant mixture with ethyl acetate three times. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel (amino-based) column chromatography to obtain the title compound of Reference Synthesis Example 40a (189 mg, yield 48%).

1. additionwas added
2. customAfter completion of the reaction
3. concentrationthe reaction solution was concentrated under reduced pressure by 4 mL and saturated sodium bicarbonate aqueous solution
4. additionwas added to the concentrated solution
5. extractionfollowed by extraction from the resultant mixture with ethyl acetate three times
6. washThe obtained organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel (amino-based) column chromatography
10. customto obtain

ORD record

ord-28141bbb4ed644f6bbc82bb8ba8a57b0

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403798B2