Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 356677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356677
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Produkt 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-tert-butoxycarbonyl-4-piperidone (10.13 g, 50.8 mmol) in anhydrous DMF (20 mL) under argon was added chlorotrimethylsilane (7.74 mL, 61.0 mmol), then anhydrous triethylamine (17.0 mL, 122 mmol) and the mixture was stirred at 80° C. for 16 h under argon. The mixture was partitioned between hexane (60 mL) and cold saturated NaHCO3 solution (50 mL). The organic layer was washed with more cold saturated NaHCO3 solution (2×30 mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 10% EtOAc/petroleum ether) to give 11.84 g (86%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 0.20 (9H, s), 1.47 (9H, s), 2.11 (2H, m), 3.52 (2H, t, J=5.8 Hz), 3.87 (2H, m), 4.80 (1H, m).

Aufarbeitung

  1. customThe mixture was partitioned between hexane (60 mL) and cold saturated NaHCO3 solution (50 mL)
  2. washThe organic layer was washed with more cold saturated NaHCO3 solution (2×30 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 10% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-9ac35e0d601c4ea7a34f4647651f25f0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837715

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