Water → tert-Butyl 8-methyl-2-oxo-1,5,7,8-tetrahydro-1,6-naphthyridine-6(2H)-carboxylate

HRID 467831

Reaktionsgleichung

Reaktionsgleichung von HRID 467831
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.N1CCCC1.O.[C:22]([NH2:26])(=[O:25])[C:23]#[CH:24]>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:7]2[NH:26][C:22](=[O:25])[CH:23]=[CH:24][C:6]=2[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 31268PyrrolidineHCID 101445PropynamideHCID 22644642tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate

Produkt 1

HCID 68313489tert-Butyl 8-methyl-2-oxo-1,5,7,8-tetrahydro-1,6-naphthyridine-6(2H)-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate (commercially available from Ryan Scientific, Mt. Pleasant, S.C.)(1.7 g, 7.97 mmol) and pyrrolidine (1.3 mL, 15.94 mmol) were dissolved in toluene (9 mL), and the solution was heated under reflux, with the removal of water under Dean-Stark conditions, for 5 hours. The solution was then cooled to room temperature and propiolamide (prepared as described in EP 1813606)(1.1 g, 15.94 mmol) was added. The reaction mixture thus obtained was heated overnight under reflux. The reaction mixture was concentrated, and the residue was purified by flash chromatography on silica gel eluting with 0% to 10% MeOH in DCM to give the title compound (2.1 g, 55% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (3H, d, J=7.04 Hz), 1.52 (9H, s), 3.37-3.44 (1H, m), 3.77-3.84 (1H, m), 4.12-4.17 (1H, m), 6.48 (1H, d, J=9.39 Hz), 7.21 (1H, d, J=9.39 Hz) ppm; LC/MS m/z: 265 (M+1).

Aufarbeitung

  1. temperaturethe solution was heated
  2. customThe reaction mixture thus obtained
  3. temperaturewas heated overnight
  4. temperatureunder reflux
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified by flash chromatography on silica gel eluting with 0% to 10% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-0828cfbbe8e243a38a9d1a45bbe63c4d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623885B2

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