Ethyl Acetate → Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate

HRID 356678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356678
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([O:14][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([F:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724933SelectfluorHCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 10560711Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-(trimethylsilyloxy)pyridine (400 g, 14.7 mmol) in anhydrous acetonitrile (160 mL) under nitrogen was added Selectfluor™ reagent (5.74 g, 16.2 mmol) and the mixture was stirred for 75 min. The mixture was poured into ethyl acetate (600 mL), washed with diluted brine (300 mL), then saturated NaCl solution (100 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (alumina, 0-5% MeOH/EtOAc) to afford 2.91 g (91%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.50 (9H, s), 2.52-2.64 (2H, m), 3.22-3.38 (2H, m), 4.18 (1H, m), 4.45 (1H, m), 4.83 (1H, m).

Aufarbeitung

  1. washwashed with diluted brine (300 mL)
  2. dry with materialsaturated NaCl solution (100 mL), dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (alumina, 0-5% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4fa58d894c43445888e148156dce3409
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837715

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