Reaktionsgleichung
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][C:10]([C:18]([OH:20])=[O:19])=[N:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:17][CH2:16]1.[O:21]1[CH2:24][C:23](=[O:25])[CH2:22]1>C1COCC1>[CH:15]1([CH2:14][O:13][C:12]2[N:11]=[C:10]([C:18]([OH:20])=[O:19])[CH:9]=[CH:8][C:7]=2[C:23]2([OH:25])[CH2:24][O:21][CH2:22]2)[CH2:17][CH2:16]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Under a nitrogen atmosphere, n-BuLi (3.23 mL, 5.6 mmol) was added dropwise to a solution of 5-bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 9 d, 1.1 g, 4.0 mmol) in THF (50 mL) at −78° C. and stirred for 1 h at this temperature. Then a solution of oxetan-3-one (CAN 6704-31-0, 0.73 g, 10 mmol) in THF (5 mL) was added at −78° C. The reaction mixture was stirred for 1 h at room temperature and quenched with aq. NH4Cl solution. The pH was adjusted to 2 with conc. HCl. The mixture was extracted with ethyl acetate (3×50 mL), the organic layers were combined, washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by chromatography over silica gel using petroleum ether/ethyl acetate=1/1 to give the title compound (0.13 g, 30.8%) as a yellow solid; MS (EI): m/e=266.1 [M+H]+.
Aufarbeitung
- stirringThe reaction mixture was stirred for 1 h at room temperature
- customquenched with aq. NH4Cl solution
- extractionThe mixture was extracted with ethyl acetate (3×50 mL)
- washwashed with brine (2×50 mL)
- dry with materialdried over Na2SO4
- customThe solvent was removed under reduced pressure
- customthe crude product was purified by chromatography over silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-3d362ccf74844d25a3489940939eca1c
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321727B2
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