N-methoxy-N-methylcycloheptanecarboxamide → Cycloheptyl(3-pyridinyl)methanone
Reaktionsgleichung
CON(C)[C:4]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[Li][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>CCOCC>[CH:6]1([C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%).
Aufarbeitung
- customquenched by addition of aqueous saturated NH4Cl
- temperatureto warm to room temperature
- additiondiluted with ether
- customThe layers were separated
- extractionthe aqueous phase was extracted 3 times with ether
- washCombined organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customAfter purification by chromatography on silica gel (CH2Cl2)
Quellen und Nachweise
- ORD-Eintrag
- ord-0f24c4cbb8bd417592cd9710636e0e75
- Quelldatensatz
- uspto-grants-2008_04
- Patentnummer
- US07361668B2
Notizen zur Reaktion
Wird geladen…