Trifluoroacetic anhydride → Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate

HRID 526926

Reaktionsgleichung

Reaktionsgleichung von HRID 526926
[C:1]([CH:4]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)[NH2:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([CH:4]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])#[N:2]

Komponenten

5

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 67286514Tert-butyl 2-carbamoyl-4,4-difluoropiperidine-1-carboxylate2×

Produkt 1

HCID 67284864Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-carbamoyl-4,4-difluoro-piperidine-1-carboxylate, 13g, (1.72 g, 6.51 mmol) in CH2Cl2 (50 mL) was added was N,N-triethylamine (2.03 mL, 14.61 mmol) followed by the dropwise addition of (2,2,2-trifluoroacetyl)-2,2,2-trifluoroacetate (1.02 mL, 7.32 mmol). After 15 minutes, the mixture was diluted with aqueous saturated NaHCO3 solution and the layers were separated. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated to dryness. The crude residue was passed through a plug of silica gel and eluted with 10-30% EtOAc/hexanes to afford the desired product, 13h.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. washeluted with 10-30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ceb5fbefd49c41c19d987aa9b349c68a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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