1-(tert-Butoxycarbonyl)piperidine-4-carboxamide → Tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate
Reaktionsgleichung
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:13]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=[O:15])[NH2:14]>CN1C(=O)N(C)CCC1>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:13]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[O:15][CH:2]=2)=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 145 °C
Versuchsvorschrift
2-Bromo-1-[4-(methylsulfanyl)phenyl]ethanone (5 g, 19.15 mmol) and tert-butyl 4-carbamoylpiperidine-1-carboxylate (4.37 g, 19.15 mmol) were dissolved in DMPU (40.8 mL) and heated to 145° C. for 15 min. The resulting solution was then cooled to room temperature, partitioned between aqueous LiCl and ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo. The resulting crude oil was purified using silica gel chromatography (300 g, using 20-80% ethyl acetate in hexane gradient) to yield 1.8 g of the desired product as a yellow oil. LCMS (M+1)=375.40
Aufarbeitung
- temperatureThe resulting solution was then cooled to room temperature
- custompartitioned between aqueous LiCl and ethyl acetate
- dry with materialThe combined organics were dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe resulting crude oil was purified
Quellen und Nachweise
- ORD-Eintrag
- ord-5c00385fa3474bff98ae15ed7735f3ed
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09193697B2
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