Diisopropylethylamine → [1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanone

HRID 220207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220207
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O-:19])=O)[CH2:12]1)(=[O:10])=[O:9].[Li+].[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[CH:25]=[CH:26][CH:27]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([N:29]2[CH2:30][CH2:31][CH2:32][CH:28]2[C:24]2[CH:23]=[C:22]([CH3:21])[CH:27]=[CH:26][CH:25]=2)=[O:19])[CH2:12]1)(=[O:9])=[O:10]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 35440982-(3-Methylphenyl)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67131265Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate

Produkt 1

HCID 57822305[1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanoneAusbeute 23,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 22350042dichloromethane N,N-dimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution 0.1 g Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate (0.32 mmol) in DMF: DCM (3:1) was added 0.047 g 2-(3-methyl phenyl)-pyrrolidine (0.29 mmol) and 0.27 mL DIPEA (1.6 mmol). The mixture was stirred for 10 minutes at room temperature and 0.147 g HATU (0.38 mmol) was added. The mixture was stirred overnight at room temperature, diluted with 15 mL brine and extracted with ethyl acetate (3×10 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to dryness to obtain the crude product which was further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane to yield 0.03 g (20.8%) of the title compound. (MH+) 447.07.

Aufarbeitung

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure to dryness
  6. customto obtain the crude product which
  7. customwas further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-eaaebfd08dca4d62948c694e4235ded4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202888B2

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