Triethylamine → 1-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][CH:11]=[CH:10][CH2:9]1.CS([Cl:21])(=O)=O.[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.N1CC[CH:32]([OH:35])CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][C:11]([CH2:22][N:24]2[CH2:27][CH2:28][CH:32]([OH:35])[CH2:26][CH2:25]2)=[CH:10][CH2:9]1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a cold (0° C.) CH2Cl2 (1 mL) solution of Example 1A (61 mg, 0.2 mmol), methanesulfonyl chloride (0.017 mL, 0.22 mmol) and triethylamine (0.035 mL, 0.25 mmol) were added. After it was stirred at 0° C. for five minutes, more triethylamine (0.035 mL, 0.25 mmol) and piperidin-4-ol (25 mg, 0.24 mmol) were added to the reaction mixture. The reaction was allowed to warm from 0° C. to room temperature overnight. It was diluted with CH2Cl2, washed with water and brine, dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (54 mg, 69%). MS (DCI) m/z 386 (M+H)+.
Aufarbeitung
- temperatureto warm from 0° C. to room temperature overnight
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- custompurified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)
Quellen und Nachweise
- ORD-Eintrag
- ord-ced110350a19409e837d9918ca383962
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07834012B2
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