1,8-Diazabicyclo(5.4.0)undec-7-ene → cis-[(Methylethyl)sulfonyl](2-phenylcyclopentyl)amine
Reaktionsgleichung
[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.[CH:24]([S:27](Cl)(=[O:29])=[O:28])([CH3:26])[CH3:25]>C(Cl)Cl>[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:27]([CH:24]([CH3:26])[CH3:25])(=[O:29])=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
(+,−) Cis-2-Phenyl-cyclopentylamine (0.43 g, 2.7 mmol, from preparations 5 or 7) was dissolved in 15 mL of methylene chloride and cooled to 0° C. under nitrogen. 0.52 mL (3.5 mmol) of DBU was added followed by 0.39 mL (3.5 mmol) of isopropylsulfonyl chloride. Stirring was allowed to continue for 3 days while warming to room temperature. The reaction was washed with 1N HCl and the organic phase dried over sodium sulfate. Filtered, and concentrated in vacuo to a crude brown solid which was a 4:1 mixture of cis:trans by NMR. The isomers were purified by radial chromatography eluting with methylene chloride. 195 mg (27%) of the title compound (cis isomer) was isolated as a white solid as well as 15 mg of the more polar trans isomer. The NMR was consistent with the assigned structure.
Aufarbeitung
- temperaturewhile warming to room temperature
- washThe reaction was washed with 1N HCl
- dry with materialthe organic phase dried over sodium sulfate
- filtrationFiltered
- concentrationconcentrated in vacuo to a crude brown solid which
- additiona 4:1 mixture of cis
- customThe isomers were purified by radial chromatography
- washeluting with methylene chloride
Quellen und Nachweise
- ORD-Eintrag
- ord-41391b6d4e0d4dcea3f489f66926d32b
- Quelldatensatz
- uspto-grants-2003_10
- Patentnummer
- US06639107B1
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