Trifluoroacetic acid → Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate

HRID 851943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851943
[C:1]([OH:7])(C(F)(F)F)=[O:2].[CH2:8]([N:15]1[CH:20]([C:21]([O:23]C(C)(C)C)=O)[CH2:19][CH2:18][CH2:17][NH:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:28](N(CC)CC)C>C(Cl)Cl>[O:23]=[C:21]([CH:20]1[CH2:19][CH2:18][CH2:17][NH:16][N:15]1[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:1]([O:7][CH3:28])=[O:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 18470069Tert-butyl 2-benzylperhydropyridazinecarboxylate

Produkt 1

HCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetateAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

20% TFA in CH2Cl2 was cooled to 0° C. and added dropwise to a solution of tert-butyl 2-benzylperhydropyridazinecarboxylate (13.34 g, 41.7 mmol) in 10 ml CH2Cl2. The mixture was stirred overnight. At this time, the mixture was cooled to 0° C. and 12.66 ml (125 mmol) triethylamine was added, followed by addition dropwise of methyl oxalyl chloride (5.62, 45.9 mmol) in 5 ml CH2Cl2. The mixture was allowed to stirred 2 hours at 0° C. and warmed up to room temperature overnight. The reaction was diluted with addition of CH2Cl2 and washed with water. The organic layer was dried over MgSO4, and filtered and concentrated. The crude product was further purified by silica chromatography to yield 9.2 g (72.4% yield) product as clear oil. 1H NMR (CDCl3, 400 MHz): δ 1.72 (m, 4H); 2.85 (m, 1H); 3.12 (m, 1H); 3.67 (s, 3H); 4.15 (m, 1H); 4.35 (m, 1H); 5.20 (m, 2H); 7.35 (m, 5H)

Aufarbeitung

  1. stirringto stirred 2 hours at 0° C.
  2. temperaturewarmed up to room temperature overnight
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was further purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-871fdc16df6543e5919d97f5200c76e3
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253169B2

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