Trifluoromethanesulfonic anhydride → 1-(tert-Butyl) 3-ethyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

HRID 1744684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744684
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O=[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][C:18]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:5])=[O:4]

Komponenten

5

Edukt 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Produkt 1

HCID 222284091-(tert-Butyl) 3-ethyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1,3(2H)-dicarboxylateAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (15.5 mL, 92.0 mmol) was added over approximately 0.1 h, via syringe, to a stirred solution of the product of step B (33.8 g, 84.0 mmol) and N,N-diisopropylethylamine (17.6 mL, 101.0 mmol) in methylene chloride (300 mL) at −78° C. After allowing to warm to ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium bicarbonate, poured into water and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent) gave the title compound as an amber colored oil (23.0 g).

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. additionpoured into water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-f48f4b34b01048c8b248043c14281c23
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015235B2

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