Triethylamine → 1-[2,4-Bis(trifluoromethyl)benzyl]-4-(hydroxymethyl)piperidin-2-one
Reaktionsgleichung
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](O)=[O:13])[CH2:8][C:7]1=[O:15].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][C:7]1=[O:15]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid (16.8 g) and triethylamine (9.8 mL) in tetrahydrofuran (200 mL) was added ethyl chloroformate (8.0 mL) under cooling to 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 1 hr under cooling to 0° C., sodium borohydride (5.18 g) was added, and the mixture was further stirred at 30° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (10.9 g).
Aufarbeitung
- temperatureunder cooling to 0° C.
- stirringthe mixture was further stirred at 30° C. overnight
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-985be7839fce482db320661b9f863cce
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08772277B2
Notizen zur Reaktion
Wird geladen…