Dichloromethane → N-{2-(6-oxabicyclo[3.1.0]hex-2-yloxy)phenyl}acetamide

HRID 965890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965890
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](=[O:16])[CH3:15])[CH2:5][CH2:4][CH:3]=[CH:2]1.ClCCl.C([O:24]C)(C)(C)C>>[CH:2]12[O:24][CH:3]1[CH2:4][CH2:5][CH:1]2[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15]

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 15413tert-Butyl methyl etherHCID 22313646N-[2-(2-cyclopenten-1-yloxy)phenyl]acetamide

Produkt 1

HCID 22313665N-{2-(6-oxabicyclo[3.1.0]hex-2-yloxy)phenyl}acetamideAusbeute 58 %

Versuchsvorschrift

To an ice bath cooled solution of N-[2-(2-cyclopenten-1-yloxy)phenyl]acetamide (149 mg, 686 μmol, 1.0 equiv.) in dichloromethane (4 ml) m-chloroperbenzoic acid (85 proc.; 146 μmol, 1.1 equiv.) was added. After stirring overnight with slowly warming up to an ambient temperature the reaction mixture was diluted by tertbutyl(methyl)ether, washed successively by a sat. sodium bisulfate solution, 5 proc. sodium hydroxide and brine and dried over sodium sulfate. Evaporation of the solvent and flash chromatography on silica gel (ethyl acetate/heptane, 2:3 continued to ethyl acetate) yielded 93 mg (58%) of the subtitle compound as a mixture of the trans, (minor) and the cis (major) diastereoisomeric epoxides as a pale yellow oil. The cis/trans ratio was determined as 2:1 by 1H-NMR.

Aufarbeitung

  1. additionwas added
  2. washwashed successively by a sat. sodium bisulfate solution, 5 proc
  3. dry with materialsodium hydroxide and brine and dried over sodium sulfate
  4. customEvaporation of the solvent and flash chromatography on silica gel (ethyl acetate/heptane, 2:3 continued to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8e3a00510c964242b95e1cd0ea4cd95f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951874B2

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