Potassium Carbonate → tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 727088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727088
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH:18]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH:16]=[C:17]([C:20]#[CH:21])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 18942192tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium carbonate (1.0 g, 7.2 mmol) was added to a solution of 1-tert-butoxycarbonyl-4-trimethylsilylethynyl- 1,2,3,6-tetrahydropyridine (44.9 g, 16 lmmol) in methanol (250 ml) under a nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours. The solution was evaporated in vacuo without heating. The residue was dissolved in ether (250 ml), washed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml) before drying (MgSO4) and evaporation in vacuo to give the title compound as a white waxy solid (30.0 g, 90%); δH (CDCl3) 1.46 (9H, s, OC(CH3)3), 2.24-2.26 (2H, m, tetrahydropyridinyl CH2), 2.89 (1H, s, ethynyl CH), 3.49 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.95-3.97 (2H, m, tetrahydropyridinyl CH2) and 6.10 (1H, s, tetrahydropyridinyl CH).

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. temperaturewithout heating
  3. dissolutionThe residue was dissolved in ether (250 ml)
  4. washwashed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml)
  5. custombefore drying
  6. custom(MgSO4) and evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e336d67b6f634052b07637b345e8cefb
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712285

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