Methylenecyclohexane → 1-[(4-methylphenyl)sulfonyl]-1-Azaspiro[2.5]octane

HRID 1023828

Reaktionsgleichung

Reaktionsgleichung von HRID 1023828
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11]Cl)(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:13]=[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>CC#N>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C:14]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14502MethylenecyclohexaneHCID 31388TosylchloramideHCID 17977687Phenyltrimethylammonium bromide dibromide

Produkt 1

HCID 111497721-[(4-methylphenyl)sulfonyl]-1-Azaspiro[2.5]octaneAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred suspension of dried Chloramine-T (5.10 g, 20.76 mmol) in CH3CN (100 mL) under a nitrogen atmosphere methylenecyclohexane (9.98 g, 104 mmol) was added. Phenyltrimethylammonium tribromide (7.80 g, 20.76 mmol) was added in three portions over 10 min. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed on silica gel with an ISCO Combiflash using EtOAc/hexanes (5-30% gradient) to afford the title compound as a white solid (2.66 g).

Aufarbeitung

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed on silica gel with an ISCO Combiflash

Quellen und Nachweise

ORD-Eintrag
ord-9d61fe0b5e3049a380a1f5b4ab11c292
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722727B2

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